N-bromobutanimide → 5-(Bromomethyl)-3-phenyl-2,1-benzisoxazole

Participants

Reaction Steps

A mixture of 11.7 g (0.05 g mole) of 5-methyl-3-phenyl-2,1-benzisoxazole, 10.0 g (0.056 mole) of N-bromosuccinimide and 0.1 g of dibenzoylperoxide in 200 ml of carbon tetrachloride was heated at reflux under illumination by a flood lamp for 2.5 hr. The mixture was filtered and the filtrate was washed with 5% sodium hydroxide, dried over sodium sulfate and concentrated to give a solid as residue. This solid was recrystallized twice from 2-propanol to yield 9.5 g (59%) of crystals, m.p. 130° C. (with decomposition).

Provenance & Evidence