Methyl alpha-bromo-2-chlorophenylacetate Chemical Properties

Boiling point:

281 °C

Density 

1.567

refractive index 

1.5630 to 1.5670

Flash point:

124 °C

storage temp. 

Refrigerator

solubility 

Dichloromethane, Ether, Ethyl Acetate, Methanol

form 

Solid

color 

Light Beige

Safety Information

RIDADR 

UN 3265 8/PG II

HS Code 

2916.39.7900

HazardClass 

8

PackingGroup 

II

Methyl alpha-bromo-2-chlorophenylacetate Usage And Synthesis

Chemical Properties

Light-Yellow Oil

Uses

Methyl α-Bromo-2-chlorophenylacetate (cas# 85259-19-4) is a compound useful in organic synthesis.

Synthesis

General procedure for the synthesis of α-bromo-2-chlorophenylacetic acid methyl ester from o-chlorophenylacetic acid methyl ester: N-bromosuccinimide (1.04 g, 5.84 mmol) and azobisisobutyronitrile (43 mg) were sequentially added to a stirred solution of methyl 2-chlorophenylacetate (0.86 mL, 5.31 mmol) in dichloromethane (10.2 mL, 159 mmol). The reaction mixture was stirred at 100 °C for 16 h under argon protection. After completion of the reaction, the mixture was cooled to room temperature, diluted with ether and filtered. The filtrate was concentrated under reduced pressure to remove the solvent to give an oily residue containing succinimide (456 mg), which was diluted with heptane and filtered again. Finally, the solvent was removed by distillation under reduced pressure to afford methyl α-bromo-2-chlorophenylacetate (1.38 g, 4.56 mmol) in 86% yield. The product was characterized by 1H NMR (500 MHz, CDCl3): δ 7.69 (dd, J = 7.6, 1.8 Hz, 1H), 7.31 (dd, J = 7.6, 1.7 Hz, 1H), 7.24 (td, J = 7.6, 1.7 Hz, 1H), 7.21 (dd, J = 7.5, 1.8 Hz, 1H), 5.84 (s 1H), 3.74 (s, 3H).

References

[1] Patent: WO2018/149856, 2018, A1. Location in patent: Paragraph 93-94
[2] Patent: WO2018/149853, 2018, A1. Location in patent: Page/Page column 96
[3] Angewandte Chemie - International Edition, 2013, vol. 52, # 16, p. 4440 - 4444
[4] Angew. Chem., 2013, vol. 125, # 16, p. 4536 - 4540,5
[5] Journal of Medicinal Chemistry, 1993, vol. 36, # 23, p. 3738 - 3742

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