N-bromobutanimide → 3-(Bromomethyl)-2,4-dichloro-1,1'-biphenyl

Participants

Reaction Steps

A stirred solution of 10.6 g (0.045 mole) of 2,4-dichloro-3-methyl[1,1'-biphenyl] and 8.0 g (0.045 mole) of N-bromosuccinimide in 100 ml of carbon tetrachloride was irradiated with a 250 watt infra-red lamp for 4 hours. The reaction mixture was allowed to reflux from the heat of the lamp during the 4 hour period. The reaction mixture was filtered and the filter cake was washed with one portion of 100 ml of carbon tetrachloride. The wash and filtrate were combined and washed with one portion of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate, filtered and the filtrate concentrated under reduced pressure to give 14.1 g of 3-bromomethyl-2,4-dichloro[1,1'-biphenyl]. The nmr spectrum was consistent with the proposed structure.

Provenance & Evidence