Benzoyl Peroxide → HCID 14835355, compound

Participants

Reaction Steps

A mixture of 1.9 g (0.0085 mole) of 6-ethyl-3-phenyl-2,1-benzisoxazole, 1.5 g (0.0087 mole) of N-bromosuccinimide and a few crystals of dibenzoyl peroxide in 100 ml of carbon tetrachloride was heated at reflux for 2 hr under floodlight illumination and under an argon atmosphere. The cooled reaction mixture was filtered, and the filtrate was washed twice with 100 ml portions of 10% sodium bicarbonate solution, once with water (100 ml) and dried over sodium sulfate. The sodium sulfate was removed by filtration and the filtrate was concentrated to a dark brown oil which solidified upon standing. The solid was purified by chromatography (3.5×60 cm glass column; 180 g of silica gel; benzene). Fractions containing the title compound were combined and the solvent was evaporated under reduced pressure to give a viscous oil which solidified upon standing. The solid was recrystallized from diethyl ether-petroleum ether (30°-60° C.) to give 1.7 g (65%) of mustard yellow crystals, m.p. 99°-102° C.

Provenance & Evidence