Alpha-Methylstyrene → (3-bromoprop-1-en-2-yl)benzene

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Reaction Steps

A mixture of 2-phenylprop-1-ene (14.16 g, 0.12 mol), N-bromosuccinimide (13.5 g, 72 mmol) and α,α'-azoisobutyronitrile (1.5 mg) in carbon tetrachloride (7.5 mL) was placed in a pre-heated oil bath at 170° C. (the internal temperature rose to 110° C.). The slurry was stirred vigorously at this temperature for 2 h. and was then allowed to cool to ambient temperature. The mixture was filtered, washing with carbon tetrachloride, and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with hexane to give the title compound as an oil (320 mg). 1H NMR (250 MHz, CDCl3) δ(7.85-7.81 (2 H, m), 7.75-7.63 (3 H, m), 5.89 (1 H, s), 5.82 (1 H, s), and 4.72 (2 H, s).

Provenance & Evidence