N-bromobutanimide → Tert-butyl 2-[4-(bromomethyl)phenyl]-5,5,5-trifluoropentanoate

Participants

Reaction Steps

540 mg (1.79 mmol) of tert-butyl 5,5,5-trifluoro-2-(4-methylphenyl)pentanoate, 333.8 mg (1.78 mmol) of N-bromosuccinimide and 14.7 mg (0.09 mmol) of 2,2′-azobis-2-methylpropionitrile in 10 ml of carbon tetrachloride were stirred under reflux for 2 h. After the reaction had gone to completion, the succinimide was filtered off and the filter residue was washed with dichloromethane. The filtrate was concentrated under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 659 mg (1.72 mmol, 97% of theory) of a yellowish oil.

Provenance & Evidence