4-BROMO-1-BROMOMETHYL-2-CHLORO-BENZENE Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

liquid

color 

Colourless

Safety Information

RIDADR 

3265

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

2903998090

4-BROMO-1-BROMOMETHYL-2-CHLORO-BENZENE Usage And Synthesis

Uses

4-Bromo-1-bromomethyl-2-chlorobenzene is used in the preparation of selective aldose reductase inhibitors.

Synthesis

To a solution of (4-bromo-2-chlorophenyl)methanol (2.80 g, 12.67 mmol) in dichloromethane (60.0 mL) was added sequentially carbon tetrabromide (4.41 g, 13.30 mmol) and triphenylphosphine (3.48 g, 13.30 mmol) under argon protection and at 0 °C. The reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, the mixture was concentrated under reduced pressure and the resulting crude product was purified by fast column chromatography (eluent: hexane solution of 10% ethyl acetate) to afford 2-chloro-4-bromobenzyl bromide as a colorless oil (3.59 g, 100% yield).1H NMR (400 MHz, CDCl3): δ 4.53 (s, 2H), 7.29 (d, J = 8.2 Hz. 1H), 7.39 (dd, J = 8.2, 1.9 Hz, 1H), 7.56 (d, J = 1.9 Hz, 1H).

References

[1] Patent: WO2004/74270, 2004, A2. Location in patent: Page 175
[2] Patent: WO2006/18725, 2006, A1. Location in patent: Page/Page column 235-236
[3] Patent: WO2008/18827, 2008, A1. Location in patent: Page/Page column 65-66
[4] Patent: WO2010/15652, 2010, A2. Location in patent: Page/Page column 68
[5] Tetrahedron Letters, 2016, vol. 57, # 3, p. 449 - 451