Benzoyl Peroxide → Ethyl 3-Bromomethyl-5-chlorobenzo[b]thiophene-2-carboxylate

Participants

Reaction Steps

A mixture of ethyl 5-chloro-3-methyl-benzo[b]thiophene-2-carboxylate (9.0 g, 0.035 mol), N-bromosuccinimide (6.53 g, 0.037 mol) and benzoyl peroxide (130 mg) in carbon tetrachloride (150 ml) was refluxed and illuminated with a sunlamp for 2 hours. The resulting suspension was cooled, filtered and the filter cake was triturated with methanol to give 9.9 g (85%) of the methanol-insoluble ethyl 3-bromomethyl-5-chlorobenzo-[b]thiophene-2-carboxylate: mp 148°-150° C.

Provenance & Evidence