Methyl alpha-bromo-2-chlorophenylacetate

Methyl alpha-bromo-2-chlorophenylacetate Property

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

RIDADR 

UN 3265 8/PG II

HS Code 

2916.39.7900

HazardClass 

8

PackingGroup 

II

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H290May be corrosive to metals

H314Causes severe skin burns and eye damage

Precautionary statements

P234Keep only in original container.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P363Wash contaminated clothing before reuse.

P390Absorb spillage to prevent material damage.

P405Store locked up.

P406Store in corrosive resistant/… container with a resistant inner liner.

P501Dispose of contents/container to..…

Methyl alpha-bromo-2-chlorophenylacetate Chemical Properties,Usage,Production

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