N-bromobutanimide → 1,2-Benzisoxazole, 6-bromo-3-(bromomethyl)-

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Reaction Steps

A mixture of 6-bromo-3-methyl-1,2-benzisoxazole (675 mg), N-bromosuccinimide (642 mg) and 1,1′-azobis(cyclohexanecarbonitrile) (90 mg) in carbon tetrachloride (7 ml) was irradiated using a 300W lamp at reflux under nitrogen for 40 h. On cooling the precipitate was removed by filtration, the solvent was evaporated and the residue was purified by flash chromatography on a silica column (4 cm diam) eluting with a cyclohexane-ethyl acetate gradient (49:1 to 24:1) to give the title compound as a pale yellow solid (350 mg).

Provenance & Evidence