4
Journal of Chemical Research 00(0)
grateful for financial support from the National Natural Science
Foundation of China (21703061), the Natural Science Foundation
of Hunan Province (2017JJ3081), and the Open Project Program of
Key Laboratory of Theoretical Organic Chemistry and Functional
Molecule, Ministry of Education (E21744).
CDCl3): δ 8.27 (d, J=8.5Hz, 2H), 7.82 (d, J=8.0Hz, 2H);
13C NMR (125.76MHz, CDCl3): δ 167.6, 136.5 (q, JC-
F =32.7Hz), 136.2, 131.6, 126.1 (d, JC-F =3.8Hz), 123.2 (q,
JC-F =272.7Hz). GC-MS (EI, 70eV): m/z=208 (M+).32
4-Acetylbenzoyl chloride (2h): White solid, yield 76%
(2.96mmol, 541mg); 1H NMR (500MHz, CDCl3): δ 8.15–
8.13 (m, 2H), 8.00–7.99 (m, 2H), 2.60 (s, 3H); 13C NMR
(125.76MHz, CDCl3): δ 197.0, 167.9, 141.8, 136.5, 131.5,
128.6, 27.0. GC-MS (EI, 70eV): m/z=182 (M+).30
ORCID iD
Jing Xiao
Supplemental material
4-Vinylbenzoyl chloride (2i): Light yellow oil, yield
81% (3.16mmol, 526mg); 1H NMR (500MHz, CDCl3): δ
8.02–8.01 (m, 2H), 7.47–7.46 (m, 2H), 6.77–6.71 (m, 1H),
5.93 (d, J=17.5Hz, 1H), 5.49 (d, J=11.0Hz, 1H); 13C
NMR (125.76MHz, CDCl3): δ 167.8, 144.4, 135.4, 131.9,
131.9, 126.6, 118.6. GC-MS (EI, 70eV): m/z=166 (M+).33
2-Naphthoyl chloride (2j): White solid, yield 70%
(2.73mmol, 520mg); 1H NMR (500MHz, CDCl3): δ 8.76 (s,
1H), 8.08–8.02 (m, 2H), 7.93 (d, J=8.5Hz, 2H), 7.73–7.69
(m, 1H), 7.65–7.62 (m, 1H); 13C NMR (125.76MHz, CDCl3):
δ 168.5, 136.4, 134.8, 132.3, 130.4, 130.1, 129.9, 128.9,
127.9, 127.5, 125.3. GC-MS (EI, 70eV): m/z=190 (M+).34
Cinnamoyl chloride (2k): White solid, yield 61%
Supplemental material for this article is available online.
References
1. Patai S (ed.). The chemistry of acyl halides. London:
Interscience,1972.
2. El-Faham A and Albericio F. Chem Rev 2011; 111: 6557.
3. Ottenheijm HCJ and Tijhuis MW. Org Synth 1983; 61: 1.
4. Lee JB. J Am Chem Soc 1966; 88: 3440.
5. Adams R, Wirth WV and French HE. J Am Chem Soc 1918;
40: 424.
6. Adams R and Ulich LH. J Am Chem Soc 1920; 42: 599.
7. Carpino LA, Cohen BJ Jr KES, Sadat-Aalaee SY, et al. J Org
Chem 1986; 51: 3732.
8. Meyer H. Monatshefte fur. Chem 1901; 22: 415.
9. Malapit CA, Ichiishi N and Sanford MS. Org Lett 2017; 19:
4142.
10. Zhang LH, Chung JC, Costello TD, et al. J Org Chem 1997;
62: 2466.
1
(2.38mmol, 396mg); H NMR (500MHz, CDCl3): δ 7.87
(d, J=15.5Hz, 1H), 7.61–7.59 (m, 2H), 7.53–7.45 (m, 3H),
6.68 (d, 16.0Hz, 1H); 13C NMR (125.76MHz, CDCl3): δ
166.2, 150.8, 133.0, 132.1, 129.3, 129.1, 122.3. GC-MS
(EI, 70eV): m/z=166 (M+).35
2-(p-Tolyl)acetyl chloride (2l): White oil, yield 65%
(2.54mmol, 427mg); 1H NMR (500MHz, CDCl3): δ 7.06–
7.01 (m, 4H), 3.95 (s, 2H), 2.22 (s, 3H); 13C NMR
(125.76MHz, CDCl3): δ 172.2, 138.1, 129.8, 129.5, 128.3,
52.8, 21.3. GC-MS (EI, 70eV): m/z=168 (M+).36
2-Phenylpropanoyl chloride (2m): Light yellow oil,
yield 78% (3.04mmol, 513mg); 1H NMR (500MHz,
CDCl3): δ 7.45–7.42 (m, 2H), 7.40–7.37 (m, 1H), 7.35–
7.33 (m, 2H), 4.17 (q, J=7.0Hz, 1H), 1.64 (d, J=7.0Hz,
3H); 13C NMR (125.76MHz, CDCl3): δ 175.7, 137.5,
129.2, 128.3, 128.0, 57.5, 18.8. GC-MS (EI, 70eV):
m/z=168 (M+).37
3-Phenylpropanoyl chloride (2n): Colorless oil, yield
57% (2.23mmol, 375mg); 1H NMR (500MHz, CDCl3): δ
7.38–7.35 (m, 2H), 7.31–7.28 (m, 1H), 7.26–7.24 (m, 2H),
3.26 (t, J=8.0Hz, 2H), 3.06 (t, J=7.5Hz, 2H); 13C NMR
(125.76MHz, CDCl3): δ 173.1, 138.7, 128.8, 128.4, 126.9,
48.6, 31.0. GC-MS (EI, 70eV): m/z=168 (M+).19
11. Hinman RL and Locatell L Jr. J Am Chem Soc 1959; 81:
5655.
12. Bauer ST. Oil Soap 1946; 23: 1.
13. Geraskina MR, Juetten MJ and Winter AH. J Org Chem
2014; 79: 5334.
14. Eckert H and Forster B. Angew Chem In Ed 1987; 26: 894.
15. Wissner A and Grudzinskas CV. J Org Chem 1978; 43:
3972.
16. Middleton WJ. J Org Chem 1979; 44: 2291.
17. Molander GA and Alonso-Alija C. J Org Chem 1998; 63:
4366.
18. Molander GA and Harris CR. J Org Chem 1997; 62: 2944.
19. Greenberg JA and Sammakia T. J Org Chem 2017; 82:
3245.
20. Burger K, Radics G, Hennig L, et al. Monatsh Chem 2005;
136: 763.
21. Uehata K, Kimura N, Hasegawa K, et al. J Nat Prod 2013;
76: 2034.
22. Morizur JF, Irvine DJ, Rawlins JJ, et al. Macromolecules
2007; 40: 8938.
23. Scott AF and Hurley FH. J Am Chem Soc 1937; 59: 1905.
24. Pierce JS, Salsbury JM and Fredericksen JM. J Am Chem Soc
1942; 64: 1691.
25. Otania J, Kikuchi T, Higashida S, et al. J Mol Struct 2015;
1084: 28.
26. Ratkovića Z, Novaković SB, Bogdanović GA, et al. Polyhedron
2010; 29: 2311.
Hexanoyl chloride (2o): Colorless oil, yield 94%
1
(3.67mmol, 493mg); H NMR (500MHz, CDCl3): δ 2.90
(t, J=7.5Hz, 2H), 1.76–1.71 (m, 2H), 1.37–1.34 (m, 4H),
0.94–0.91 (m, 3H); 13C NMR (125.76MHz, CDCl3): δ
173.9, 47.1, 30.5, 24.8, 22.2, 13.8. GC-MS (EI, 70eV):
m/z=134 (M+).38
27. Cade JA and Gerrard W. J Chem Soc 1954; 2030.
28. Xiao J and Han LB. J Chem Res 2019; 43: 205.
29. Zhou L, Zhu Y, Jiang Y, et al. Bioorg Med Chem Lett 2017;
27: 4180.
30. Wang L, Xie YB, Huang NY, et al. ACS Catal 2016; 6: 4010.
31. Li W, Gao JJ, Zhang Y, et al. Adv Synth Catal 2011; 353:
1671.
Declaration of conflicting interests
The author(s) declared no potential conflicts of interest with
respect to the research, authorship, and/or publication of this
article.
Funding
The author(s) disclosed receipt of the following financial support 32. Quesnel JS and Arndtsen BA. J Am Chem Soc 2013; 135:
for the research, authorship, and/or publication of this article: J.X. is
16841.