865352-01-8

Basic information

• Product Name: 2-(2,2-difluoroethoxy)-6-(trifluoroMethyl)benzene-1-sulfonyl chloride
• Synonyms: 2-(2,2-difluoroethoxy)-6-(trifluoroMethyl)benzene-1-sulfonyl chloride;2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride
• CAS NO: 865352-01-8
• Molecular Formula: C₉H₆ClF₅O₃S
• Molecular Weight: 324.652156
• EINECS: -0
• Mol File: 865352-01-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 70-72 °C
• Boiling Point: 341.1±42.0 °C(Predicted)
• Appearance: /
• Density: 1.535±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-(2,2-difluoroethoxy)-6-(trifluoroMethyl)benzene-1-sulfonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2,2-difluoroethoxy)-6-(trifluoroMethyl)benzene-1-sulfonyl chloride(865352-01-8)
• EPA Substance Registry System: 2-(2,2-difluoroethoxy)-6-(trifluoroMethyl)benzene-1-sulfonyl chloride(865352-01-8)

Safety Data

• Hazardous Substances Data: 865352-01-8(Hazardous Substances Data)

Usage

General Description

2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)benzene-1-sulfonyl chloride is a chemical compound possessing several important elements, including carbon, hydrogen, oxygen, sulfur, and fluorine. This chemical, also referred to by its CAS Number 1255327-74-2, is noted for its specific structure involving both difluoroethoxy and trifluoromethyl groups, along with a benzene-based core which includes a sulfonyl chloride group. These specialized structural attributes could suggest potential applications in various industrial and scientific contexts, such as pharmaceutical synthesis, where the compound may serve specific roles in the development of new drugs. The exact properties of this chemical, such as its melting point, boiling point, density, molecular weight, and solubility, may vary depending on its specific refinement and preparation procedures.

Synthetic route

1-(2,2-difluoroethoxy)-2-(propylsulphanyl)-3-(trifluoromethyl)benzene (924647-38-1) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
With chlorine; acetic acid In water at 45 - 55℃;	100%
With chlorine; acetic acid In water at 45 - 55℃; for 2h;	98%
With chlorine In formic acid at 35 - 40℃; Solvent; Temperature;	95.3%

2-(2,2-difluoroethoxy)- 6-trifluoromethylanisole → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
With chlorine; acetic acid In water at 45 - 55℃; for 2h;	94%

C18H12F10O2S2 → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
With potassium permanganate; sulfuryl dichloride In acetonitrile at 90℃; for 1h; Concentration; Reagent/catalyst; Solvent; Temperature;	90%

1-(2,2-difluoroethoxy)-3-(trifluoromethyl)benzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Stage #1: 1-(2,2-difluoroethoxy)-3-(trifluoromethyl)benzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃; for 2h; Stage #2: With sulfuryl dichloride In tetrahydrofuran at 20℃; for 4h; Reagent/catalyst;	82%

C11H11F5OS → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
With hydrogenchloride; chlorine In water; 1,2-dichloro-ethane at 50 - 55℃; for 6h;	80.5%

C16H13F5OS → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
With hydrogenchloride; chlorine In dichloromethane; water at 30 - 40℃; for 6h;	79.3%

1-(2,2-difluoroethoxy)-2-(propylsulphanyl)-3-(trifluoromethyl)benzene (924647-38-1) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8) + propyl 2-(2,2-Difluoroethyl)-4-trifluoromethylbenzenesulfone

Conditions	Yield
With chlorine In water at 50℃; Solvent; Temperature;	A 78% B 12%

2-fluoro-6-trifluoromethyl-n-propylsulfanylbenzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium / 1,4-dioxane / Reflux 1.2: 2 h / Reflux 2.1: chlorine; acetic acid / water View Scheme

3-fluoro-trifluoromethylbenzene (401-80-9) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 - -70 °C / Inert atmosphere 1.2: 1 h / -70 °C / Inert atmosphere 2.1: sodium / 1,4-dioxane / Reflux 2.2: 2 h / Reflux 3.1: chlorine; acetic acid / water View Scheme

2-chloro-1-nitro-3-(trifluoromethyl)benzene (39974-35-1) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 50 °C 2: tetrabutyl ammonium fluoride / dimethyl sulfoxide / 3 h / 85 °C 3: sodium hydride / N,N-dimethyl-formamide 4: sodium hydrogensulfite; formic acid / 1.5 h / 23 - 37 °C View Scheme

1-nitro-2-propylthio-3-trifluoromethylbenzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrabutyl ammonium fluoride / dimethyl sulfoxide / 3 h / 85 °C 2: sodium hydride / N,N-dimethyl-formamide 3: sodium hydrogensulfite; formic acid / 1.5 h / 23 - 37 °C View Scheme

2-(3-(trifluoromethyl)phenoxy)tetrahydro-2H-pyran (896732-43-7) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: N,N,N,N,-tetramethylethylenediamine; N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -70 - 20 °C / Inert atmosphere; Large scale 1.2: 18 h / -70 - 20 °C / Large scale 2.1: hydrogenchloride / water; ethanol / 12 h / 20 °C 3.1: potassium carbonate / acetone / Reflux 4.1: acetic acid; chlorine / 2 h View Scheme
Multi-step reaction with 5 steps 1.1: isopropylamine; n-butyllithium / hexane; cyclohexane / 2 h / -78 °C / Inert atmosphere 1.2: 2 h / 25 °C 2.1: hydrogenchloride / isopropyl alcohol; water / 6 h / 82 °C 3.1: sodium iodide / isopropyl alcohol; water / 2 h / 150 °C 4.1: sodium carbonate / toluene / 3 h / 110 °C 5.1: sulfuryl dichloride; potassium permanganate / acetonitrile / 1 h / 90 °C View Scheme

2-(2-(propylthio)-3-(trifluoromethyl)phenoxy)tetrahydropyran → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water; ethanol / 12 h / 20 °C 2: potassium carbonate / acetone / Reflux 3: acetic acid; chlorine / 2 h View Scheme

3-Trifluoromethylphenol (98-17-9) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogenchloride / 1,4-dioxane / 20 °C 2.1: N,N,N,N,-tetramethylethylenediamine; N-ethyl-N,N-diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 2.5 h / -70 - 20 °C / Inert atmosphere; Large scale 2.2: 18 h / -70 - 20 °C / Large scale 3.1: hydrogenchloride / water; ethanol / 12 h / 20 °C 4.1: potassium carbonate / acetone / Reflux 5.1: acetic acid; chlorine / 2 h View Scheme
Multi-step reaction with 6 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 2 h / 25 °C 2.1: isopropylamine; n-butyllithium / hexane; cyclohexane / 2 h / -78 °C / Inert atmosphere 2.2: 2 h / 25 °C 3.1: hydrogenchloride / isopropyl alcohol; water / 6 h / 82 °C 4.1: sodium iodide / isopropyl alcohol; water / 2 h / 150 °C 5.1: sodium carbonate / toluene / 3 h / 110 °C 6.1: sulfuryl dichloride; potassium permanganate / acetonitrile / 1 h / 90 °C View Scheme

2-hydroxy-6-trifluoromethylphenyl propylsulfide → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / Reflux 2: acetic acid; chlorine / 2 h View Scheme

C12H12F3O2S(1-)*Li(1+) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / isopropyl alcohol; water / 6 h / 82 °C 2: sodium iodide / isopropyl alcohol; water / 2 h / 150 °C 3: sodium carbonate / toluene / 3 h / 110 °C 4: sulfuryl dichloride; potassium permanganate / acetonitrile / 1 h / 90 °C View Scheme

C7H5F3OS → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium iodide / isopropyl alcohol; water / 2 h / 150 °C 2: sodium carbonate / toluene / 3 h / 110 °C 3: sulfuryl dichloride; potassium permanganate / acetonitrile / 1 h / 90 °C View Scheme

1,2-dichloro-3-(trifluoromethyl)benzene (54773-19-2) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium fluoride; tetraphenylphosphonium bromide / sulfolane / 20 h / 250 - 300 °C / Autoclave 2: potassium carbonate / N,N-dimethyl-formamide / 6 h / -5 - 50 °C 3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 24 h / 20 °C / Inert atmosphere 4: hydrogenchloride; chlorine / water; 1,2-dichloro-ethane / 6 h / 50 - 55 °C View Scheme

1,2-difluoro-3-(trifluoromethyl)benzene (64248-59-5) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / -5 - 50 °C 2: sodium hydride / N,N-dimethyl-formamide; mineral oil / 24 h / 20 °C / Inert atmosphere 3: hydrogenchloride; chlorine / water; 1,2-dichloro-ethane / 6 h / 50 - 55 °C View Scheme

2-fluoro-6-trifluoromethyl-ethylsulfanylbenzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 24 h / 20 °C / Inert atmosphere 2: hydrogenchloride; chlorine / water; 1,2-dichloro-ethane / 6 h / 50 - 55 °C View Scheme

C14H10F4S → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydride / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2: hydrogenchloride; chlorine / dichloromethane; water / 6 h / 30 - 40 °C View Scheme

3-bromo-1-trifluoromethylbenzene (401-78-5) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: lithium hexamethyldisilazane / diethyl ether / 0.75 h / -78 °C 1.2: 2 h 2.1: sodium t-butanolate; copper(I) bromide / 48 h / 80 °C 3.1: formic acid; N-chloro-succinimide / water; acetonitrile / 10 °C View Scheme
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane / 0.92 h / -78 °C 1.2: 2 h / -78 - 20 °C 2.1: sodium 2.2: 48 h / 100 °C 3.1: N-chloro-succinimide; hydrogenchloride / acetonitrile; water / 20 °C View Scheme

1-bromo-2-(methylsulphanyl)-3-(trifluoromethyl)benzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium amide / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 1.2: 12 h 2.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

2-bromo-5-nitro-benzotrifluoride (367-67-9) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 6 steps 1.1: chlorine; sulfuric acid / 60 °C 2.1: ammonium chloride; zinc / water; ethanol / 3 h / Reflux 3.1: sodium nitrite; sulfuric acid / tetrahydrofuran; water / 1 h / -5 °C 3.2: 8 h 4.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -25 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 2 h / 0 - 25 °C 5.2: 12 h 6.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; sulfuric acid / 70 - 80 °C 2.1: hydrogenchloride; zinc / 5 h / 45 °C 3.1: tert.-butylnitrite / N,N-dimethyl-formamide / 2 h / Heating 4.1: isopropylmagnesium bromide / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere 4.2: Inert atmosphere 5.1: sodium amide / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 5.2: 12 h 6.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme
Multi-step reaction with 6 steps 1.1: N-Bromosuccinimide; sulfuric acid / 70 - 80 °C 2.1: hydrogenchloride; zinc / 5 h / 45 °C 3.1: tert.-butylnitrite / N,N-dimethyl-formamide / 2 h / Heating 4.1: magnesium; ethylene dibromide / tetrahydrofuran / 20 - 40 °C 4.2: 5 - 20 °C 5.1: sodium amide / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 5.2: 12 h 6.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

2-bromo-3-trifluoromethyl-5-nitrochlorobenzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions

Yield

Multi-step reaction with 5 steps 1.1: ammonium chloride; zinc / water; ethanol / 3 h / Reflux 2.1: sodium nitrite; sulfuric acid / tetrahydrofuran; water / 1 h / -5 °C 2.2: 8 h 3.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -25 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 2 h / 0 - 25 °C 4.2: 12 h 5.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

4-bromo-3-chloro-5-(trifluoromethyl)aniline (914225-58-4) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium nitrite; sulfuric acid / tetrahydrofuran; water / 1 h / -5 °C 1.2: 8 h 2.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -25 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 2 h / 0 - 25 °C 3.2: 12 h 4.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

2-bromo-1-chloro-3-(trifluoromethyl)benzene (384-16-7) → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -25 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 2 h / 0 - 25 °C 2.2: 12 h 3.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

1-chloro-2-(methylsulphanyl)-3-(trifluoromethyl)benzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl acetamide / 2 h / 0 - 25 °C 1.2: 12 h 2.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

2-bromo-3-trifluoromethyl-5-nitrobromobenzene → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 5 steps 1.1: hydrogenchloride; zinc / 5 h / 45 °C 2.1: tert.-butylnitrite / N,N-dimethyl-formamide / 2 h / Heating 3.1: isopropylmagnesium bromide / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: sodium amide / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 4.2: 12 h 5.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme
Multi-step reaction with 5 steps 1.1: hydrogenchloride; zinc / 5 h / 45 °C 2.1: tert.-butylnitrite / N,N-dimethyl-formamide / 2 h / Heating 3.1: magnesium; ethylene dibromide / tetrahydrofuran / 20 - 40 °C 3.2: 5 - 20 °C 4.1: sodium amide / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 4.2: 12 h 5.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

3,4-dibromo-5-trifluoromethylaniline → 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: tert.-butylnitrite / N,N-dimethyl-formamide / 2 h / Heating 2.1: isopropylmagnesium bromide / tetrahydrofuran / 2 h / -40 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium amide / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 3.2: 12 h 4.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme
Multi-step reaction with 4 steps 1.1: tert.-butylnitrite / N,N-dimethyl-formamide / 2 h / Heating 2.1: magnesium; ethylene dibromide / tetrahydrofuran / 20 - 40 °C 2.2: 5 - 20 °C 3.1: sodium amide / N,N-dimethyl-formamide / 2 h / 0 - 25 °C 3.2: 12 h 4.1: acetic acid; chlorine / water / 2 h / 45 - 55 °C View Scheme

2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8) + 2-fluoro-N-methylaniline (1978-38-7) → 2-(2,2-difluoroethoxy)-N-(2-fluorophenyl)-N-methyl-6-(trifluoromethyl)benzenesulfonamide

Conditions	Yield
With 3,5-Lutidine In dimethyl sulfoxide; toluene at 60 - 65℃; for 4.5h;	94.36%

2-amino-5,8-dimethoxy[1,2,4]triazolo-[1,5-c]pyrimidine (219715-62-5) + 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8) → penoxsulam

Conditions	Yield
With 3,5-Lutidine; dimethyl sulfoxide In 3,5-Lutidine at 20℃; for 8.5h; Product distribution / selectivity;	91%
With 3,5-Lutidine; dimethyl sulfoxide In acetonitrile at 20℃; for 24h; Product distribution / selectivity;	89%
With 3-Methylpyridine; N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-S,S-dimethylsulfilimine hydrochloride In acetonitrile at 8 - 48℃; for 20 - 48h; Product distribution / selectivity;	86%

5,7-dimethoxy-[1,2,4]-triazolo-[1,5-a]-pyrimidin-2-amine (13223-43-3) + 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8) → 2-(2,2-difluoroethoxy)-N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide

Conditions	Yield
With 3,5-Lutidine; dimethyl sulfoxide In acetonitrile at 35℃; for 1h;	84.9%

2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8) + 2-amino-5,7-dimethyl<1,2,4>triazolo<1,5-a>pyrimidine (7135-02-6) → 2-(2,2-difluoroethoxy)-N-(5,7-dimethyl[1,2,4]triazolo-[1,5-a]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide

Conditions	Yield
With 3,5-Lutidine; dimethyl sulfoxide In acetonitrile at 35℃; for 1h;	83.3%

2-amino-5,8-dimethoxy[1,2,4]triazolo-[1,5-c]pyrimidine (219715-62-5) + 2-(2',2'-difluoroethoxy)-6-trifluoromethylbenzene-1-sulfonyl chloride (865352-01-8) → 3-(2,2-difluoroethoxy)-N-(5,8-dimethoxy [1,2,4] triazolo[1,5-c]pyrimidin-2-yl)-cL,cL,cL-trifluorotoluene-2-sulfonamide

Conditions	Yield
With pyridine; dimethyl sulfoxide In acetonitrile Molecular sieve;	54%

Upstream product

• 493038-92-9 1,2-dibromo-3-trifluoromethylbenzene 
• 384-16-7 2-bromo-1-chloro-3-(trifluoromethyl)benzene 
• 914225-58-4 4-bromo-3-chloro-5-(trifluoromethyl)aniline 
• 914225-53-9 2-bromo-3-trifluoromethyl-5-nitro-chlorobenzene 
• 367-67-9 2-bromo-5-nitro-benzotrifluoride 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 64248-59-5 1,2-difluoro-3-(trifluoromethyl)benzene 
• 54773-19-2 1,2-dichloro-3-(trifluoromethyl)benzene 
• 98-17-9 3-Trifluoromethylphenol 
• 896732-43-7 2-(3-(trifluoromethyl)phenoxy)tetrahydro-2H-pyran 

Downstream Products

• 219714-96-2 penoxsulam 

Relevant articles and documents

Convenient Synthesis of 2-(2,2-Difluoroethoxy)-6-(trifluoromethyl)-benzenesulfonyl Chloride, A Key Building Block of Penoxsulam

A convenient and efficient three-step synthesis of 2-(2,2-difluoroethoxy)-6-(trifluoromethyl)benzenesulfonyl chloride, the key building block of penoxsulam, is described. The main features of the synthesis include a regioselective lithiation and subsequent electrophilic substitution starting from commercially available 3-bromobenzotrifluoride to provide (2-bromo-6-(trifluoromethyl)phenyl)(propyl)sulfane, then a copper-catalyzed C-O coupling to introduce the difluoroethoxy moiety and chloroxidation conditions to give the desired sulfonyl chloride.

Synthesis method of 2-(2, 2-difluoroethyoxyl)-6-trifluoromethyl benzenesulfonyl chloride

The invention discloses a synthesis method of 2-(2, 2-difluoroethyoxyl)-6-trifluoromethyl benzenesulfonyl chloride. The preparation method comprises the following steps: dissolving 2-trifluoromethyl-4-nitro-bromobenzene in sulfuric acid, adding a halogenating reagent, and reacting at 50-100 DEG C for 1-8 hours; dissolving the obtained 2-bromo-3-trifluoromethyl-5-nitro-benzene halide in a solvent, and performing reduction in a reduction system; carrying out diazotization on the obtained 3-halo-4-bromo-5-trifluoromethyl-aniline, and then carrying out decomposition on the obtained 3-halo-4-bromo-5-trifluoromethyl-aniline; carrying out Grignard reaction on the obtained 2-bromo-3-trifluoromethyl-benzene halide, and then reacting with dialkyl disulfide; carrying out etherification reaction on the obtained 2-alkylthio-3-trifluorotoluene-benzene halide and 2, 2-difluoroethanol in an organic solvent under the action of an alkali; and reacting the obtained 2-(2, 2-difluoroethoxy)-6-trifluoromethyl-phenylalkyl sulfide with chlorine gas at 10-60 DEG C for 1-5 hours. The method is short in route, mild in condition, high in yield and suitable for industrial production.

Preparation method of 2-(2,2-difluoroethyoxyl)-6-trifluoromethyl benzenesulfonyl chloride

The invention relates to the technical field of synthesis of pesticides and particularly relates to a preparation method of 2-(2,2-difluoroethyoxyl)-6-trifluoromethyl benzenesulfonyl chloride. The preparation method comprises the following steps: reacting m-trifluoromethylphenol with 3,4-dihydropyran to obtain a compound expressed as a formula (I), reacting the compound expressed as the formula (I) with n-butyl lithium and sulphur to obtain a compound expressed as a formula (II), reacting the compound expressed as the formula (II) under the action of an inorganic acid catalyst to obtain a compound expressed as a formula (III), reacting an alcoholic solution of elementary iodine or an alcoholic solution of iodide with the compound expressed as the formula (III) to obtain a compound expressed as a formula (IV), then reacting the compound expressed as the formula (IV) with carbonate and p-toluenesulfonate difluoroethanol sulfonate to obtain a compound expressed as a formula (V), and reacting the compound expressed as the formula (V) with a chlorination reagent and an oxidation reagent to obtain a final product. Through the preparation method, the generation of foul odor in the conventional synthesis process is avoided; chlorine gas with high risk is not used as the chlorination reagent; the safety in production is greatly improved.