Carbon tetrabromide → 4-(Bromomethyl)-1-chloro-2-iodobenzene

Participants

Reaction Steps

Triphenylphosphine (1.1 g) was added in portions to a solution of 4-chloro-3-iodobenzyl alcohol (1.1 g) in dichloromethane (40 ml) at 0° C. and stirring was continued for 10 minutes. Carbon tetrabromide (1.5 g) was then added in portions over 2 minutes, the reaction mixture was allowed to warm to ambient temperature and was stirred for 15 hours. The solution was added directly to a silica charged chromatography column and was eluted with dichloromethane to give 4-chloro-3-iodobenzyl bromide (1.9 g). NMR (CD3SOCD3): d 4.6 (s, 2H), 7.5 (m, 2H), 7.6 (s, 1H), 8.0 (m, 1H).

Provenance & Evidence