Benzoyl Peroxide → (3-bromoprop-1-en-2-yl)benzene

Participants

Reaction Steps

N-Bromosuccinimide (52.0 g, 292 mmol) and benzoylperoxide (2.0 g, 8.0 mmol) were added to a solution of isopropenylbenzene (82.0 g, 694 mmol) in carbon tetrachloride (200 mL). The reaction mixture was heated to reflux. After 18 h, additional N-bromosuccinimide (30.0 g, 168 mmol) was added. After 18 h, the mixture was allowed to cool to ambient temperature and the solid in the mixture was filtered off. The filtrate was concentrated and purified by vacuum distillation (95-120° C., 10 torr). The isolated mixture was purified by silica gel chromatography (100% hexanes) to give the title compound.

Provenance & Evidence