N-bromobutanimide → Methyl 4'-(bromomethyl)biphenyl-2-carboxylate

Participants

Reaction Steps

N-Bromosuccinimide (8.1 g) and azo(bisisobutyronitrile) (130 mg) were added to a solution of compound (B) (9.3 g) in carbontetrachloride (300 ml). The mixture was heated under reflux for 4 hours and then cooled to ambient temperature. Insoluble material was removed by filtration and the filtrate concentrated. The residue was purified by flash chromatography, eluting with ethyl acetate/hexane (1:9 v/v) to give methyl 4'-(bromomethyl)biphenyl-2-carboxylate (C) as a solid (10.9 g), m.p. 48°-50° C.; NMR: 3.65(s,3H), 4.55(s,2H), 7.25-7.60 complex (m,7H), 7.85(d,1H).

Provenance & Evidence