Benzoyl Peroxide → 5-(Bromomethyl)benzo[b]thiophene

Participants

Reaction Conditions

Reaction Steps

In a flask was placed 5-methyl-benzo[b]thiophene (3.64 g, 24.56 mmol) and carbon tetrachloride (75 mL). To the reaction mixture was then added N-bromosuccinimide (5.68 g, 31.92 mmol) and benzoyl peroxide (892 mg, 3.68 mmol) and it was the final solution was then heated at 76° C. for 6 h. After this time the reaction mixture was cooled to 0° C. in an ice bath and the solids were filtered off and the filterate was concentrated in vacuo and purified on an AnaLogix Intelliflash system (120 g column, 3% ethyl acetate/hexanes) to afford 5-bromomethyl-benzo[b]thiophene (5.27 g, 94%) as a yellow solid.

Provenance & Evidence