Benzoyl Peroxide → 1-Bromo-3-(bromomethyl)-2-chloro-4-fluorobenzene

Participants

Reaction Steps

A mixture of 3-bromo-2-chloro-6-fluoro-toluene (commercially available) (8.0 g), N-bromosuccinimide (“NBS”) (6.42 g) and benzoyl peroxide (catalytic amount) in carbon tetrachloride (40 ml) was heated to reflux. A 500 watt tungsten halogen lamp was used to initiate the reaction. The reaction mixture was heated to reflux and irradiated for 30 minutes. The reaction mixture was allowed to cool to ambient temperature and then filtered. The filtrate was concentrated to give a colorless oil which solidified on standing to give 1-bromo-3-bromomethyl-2-chloro-4-fluoro-benzene as an off-white solid (10.7 g). 1H-NMR (400 MHz, CDCl3): 7.58 (dd, 1H), 6.94 (t, 1H), 4.64 (d, 21-1) ppm.

Provenance & Evidence