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

Participants

Reaction Steps

A mixture of 8.70 g of 2-fluoro-4'-methylbiphenyl, 8.32 g of N-bromosuccinimide, 0.10 g of 2,2'-azobisisobutylonitrile and 150 ml of carbon tetrachloride was heat-refluxed for 5 hours. The reaction solution was washed with water, and the organic layer was concentrated. The resulting residue was purified through silica-gel column chromatography (eluent: a mixture of hexane and ethyl acetate at a ratio of 9:1) to obtain crude 2-fluoro-4'-bromomethylbiphenyl. Further, this compound was crystallized from hexane to give 4.93 g of 2-fluoro-4'-bromomethylbiphenyl.

Provenance & Evidence