N-bromobutanimide → Methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate

Participants

Reaction Steps

Methyl 2-m-tolylbenzo[d]oxazole-7-carboxylate (500 mg, 1.87 mmol), 1-bromopyrrolidine-2,5-dione (367 mg, 2.06 mmol) and benzoperoxoic acid (25.81 mg, 0.187 mmol) were added to toluene (30 mL) and the mixture was stirred at reflux overnight. The resulting mixture was evaporated, extracted with ethyl acetate (100 mL×4) and concentrated to obtain methyl 2-(3-(bromomethyl)phenyl)benzo[d]oxazole-7-carboxylate as a solid (194 mg, yield 30%). LC-MS (ESI) m/z 347 [M+1]+.

Provenance & Evidence