N-bromobutanimide → Ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 1.60 mmol) in DMF (10 mL) was added N-bromsuccinimide (284 mg, 1.60 mmol). The mixture was stirred overnight at 45° C. then cooled to room temperature and diluted with water then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography (10% ethyl acetate in hexanes) to give ethyl 2-bromo-4-cyano-5-[(2-methylpropyl)amino]benzoate (374 mg, 72.0%) as a yellow solid. MS (EI) for C14H17BrN2O2: 324 (M+).

Provenance & Evidence