N-bromobutanimide → 3-[3-(Bromomethyl)phenyl]thiophene

Participants

Reaction Steps

A stirred solution of 9.8 g (0.056 mol) of 3-(3-methylphenyl)thiophene in 250 mL of carbon tetrachloride was heated to reflux, and 0.5 g of benzoyl peroxide was added. Heating was continued, and after five minutes an additional 0.5 g of benzoyl peroxide and 10 g of N-bromosuccinimide were added. Upon complete addition, the reaction mixture was heated under reflux for an additional 2.5 hours, then cooled in an ice-water bath for one hour. The reaction mixture was filtered, and the filter cake washed with 50 mL of carbon tetrachloride. The wash and filtrate were combined, and the whole was washed with 200 mL 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 a residual oil. The residual oil was subjected to distillation under reduced pressure using a Kugelrohr distilling system to give 8.7 g of 3-(3-bromomethylphenyl)thiophene, b.p. 95°-150° C./0.1 mm.

Provenance & Evidence