Benzoyl Peroxide → 4-Cyano-3-fluorobenzyl bromide

Participants

Reaction Steps

A mixture of 2-fluoro-4-methylbenzonitrile (1 g, 7.4 mmol), benzoylperoxide (0.39 g, 1.6 mmol), and N-bromosuccinimide (1.9 g, 10.6 mmol) in carbontetrachloride (100 mL) was heated at reflux for 3 h. The resulting suspension was filtered and the filtrate diluted with dichloromethane, washed with a saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:n-hexane, 1:9) to give the title compound as a yellow oil (0.9 g, 56%).

Provenance & Evidence