4-Iodo-1-chloro-2-(4-ethoxybenzyl)benzene

Base Information

• Chemical Name: 4-Iodo-1-chloro-2-(4-ethoxybenzyl)benzene
• CAS No.: 1103738-29-9
• Molecular Formula: C15H14ClIO
• Molecular Weight: 372.633
• Mol file: 1103738-29-9.mol

Synonyms:Benzene, 1-chloro-2-[(4-ethoxyphenyl)methyl]-4-iodo-; 1-Chloro-2-(4-Ethoxybenzyl)-4-Iodobenzene; 4-(5-Iodo-2-chlorobenzyl)phenyl ethyl ether; 4-Iodo-1-chloro-2-(4-ethoxybenzyl)benzene

Chemical Property of 4-Iodo-1-chloro-2-(4-ethoxybenzyl)benzene

Chemical Property:

• Appearance/Colour: off-white solid
• Boiling Point: 411.2±40.0 °C(Predicted)
• PSA: 9.23000
• Density: 1.531±0.06 g/cm3(Predicted)
• LogP: 4.93410
• Storage Temp.: 2-8°C(protect from light)
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

1-Chloro-2-(4-ethoxybenzyl)-4-iodobenzene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Chloro-2-(4-ethoxybenzyl)-4-iodobenzene is used in the synthesis of Dapagliflozin (D185370), a sodium-glucose transporter 2 inhibitor.

Technology Process of 4-Iodo-1-chloro-2-(4-ethoxybenzyl)benzene

There total 12 articles about 4-Iodo-1-chloro-2-(4-ethoxybenzyl)benzene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.4%

(2-chloro-5-iodo-phenyl)-(4-ethoxyphenyl)methanone (1103738-26-6) → 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (1103738-29-9)

Guidance literature:

With triethylsilane; boron trifluoride diethyl etherate; In acetonitrile; at 5 - 20 ℃; for 17.5h;

Reference yield: 95.9%

2-bromomethyl-1-chloro-4-iodo-benzene (793695-85-9) + 4-bromoethoxybenzene (588-96-5) → 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (1103738-29-9)

Guidance literature:

4-bromoethoxybenzene; With iodine; magnesium; methoxybenzene; at 47 ℃; for 3.2h;

2-bromomethyl-1-chloro-4-iodo-benzene; With copper(l) iodide; at -18 - 20 ℃; for 16.2h; Temperature;

Reference yield: 67.0%

2-chloro-5-iodobenzoylchloride (281652-58-2) + Phenetole (103-73-1) → 1-chloro-2-(4-ethoxybenzyl)-4-iodobenzene (1103738-29-9)

Guidance literature:

2-chloro-5-iodobenzoylchloride; Phenetole; With aluminum (III) chloride; In dichloromethane; at -5 - 15 ℃;

at 25 - 30 ℃; for 26h;

upstream raw materials:

(2-chloro-5-iodo-phenyl)-(4-ethoxyphenyl)methanone

2-chloro-5-iodobenzoylchloride

2-chloro-5-iodobenzoic acid

Phenetole

Downstream raw materials:

(4-chloro-3-(4-ethoxybenzyl)phenyl)((3aS,5R,6S,6aS)-6-hydroxy-2,2-dimethyltetrahydrofuran[2,3-d][1,3]dioxolan-5-yl)methanone

(2S,3R,4R,5S,6R)-2-[4-chloro-3-(4-ethoxybenzyl)phenyl]-6-(methylsulfanyl)tetrahydro-2-H-pyran-3,4,5-triol

[(2S,3S,4R,5S,6R)-4,5-diacetoxy-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylthiotetrahydropyran-3-yl]acetate

acetic acid (3S,4R,5S,6S)-2,4,5-triacetoxy-6-[4-chloro-3-(4-ethoxy-benzyl)-phenyl]-tetrahydropyran-3-yl ester

Refernces

• 1、 Vaňková, Karolína,Rahm, Michal,Choutka, Jan,Pohl, Radek,Parkan, Kamil. "Facile Approach to C-Glucosides by Using a Protecting-Group-Free Hiyama Cross-Coupling Reaction: High-Yielding Dapagliflozin Synthesis". supporting information. p. 10583 - 10588. Retrieved 2021/06/25.
• 2、 Hu, Shengquan,Sun, Wuji,Wang, Yeming,Yan, Hong. "Design, synthesis and anticancer activities of halogenated Phenstatin analogs as microtubule destabilizing agent". . p. 465 - 472. Retrieved 2019/02/09.