N-bromobutanimide → 4-Bromo-3-chloro-5-(trifluoromethyl)aniline

Participants

Reaction Steps

To a mixture of 3-chloro-5-(trifluoromethyl)aniline (3.25 g, 16.6 mmol, Eq: 1.00) in dimethylsulfoxide (43.4 ml) was added N-bromosuccinimide (3.11 g, 17.4 mmol, Eq: 1.05) in 5 portions over 2.5 hr (622 mg each 30 min). 2 h after the last addition, the reaction mixture was partitioned between 10% aqueous sodium sulfite and ethyl acetate. The organic layer was washed with aqueous sat. sodium carbonate, water (3 times) and brine then adsorbed unto silica (6 g) and purified on silica gel (column 120 g, Hexane/ethyl acetate 90:10 to 65:35) to give 4.36 g (96%) of a yellow solid.

Provenance & Evidence