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

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).

1. customwas placed in a pre-heated oil bath at 170° C.
2. customrose to 110° C.
3. filtrationThe mixture was filtered
4. washwashing with carbon tetrachloride
5. customthe solvent was evaporated under reduced pressure
6. customThe residue was purified by column chromatography on silica gel
7. washeluting with hexane

ORD record

ord-ef6a11edf8b74489a796b8e82d434360

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06071927