N-bromobutanimide → HCID 136399879, compound

Participants

Reaction Steps

A mixture of 4-hydroxy-3-phenyl-isoxazolo[5,4-c]pyridine-5-carboxylic acid ethyl ester (388.1 mg, 1.37 mmol), N-bromosuccinimide (255 mg, 1.43 mmol), benzoyl peroxide (16 mg, 0.07 mmol), and carbon tetrachloride (10 ml) was refluxed for 3 h before it was cooled to room temperature and partitioned between dichloromethane and water. The organic layer was washed with saturated aqueous sodium bicarbonate solution and brine before it was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of ethyl acetate and dichloromethane to give the title compound as a white solid (432 mg): MS: (−) m/z 361.21, 363.23 (M−1, 79Br/81Br).

Provenance & Evidence