Benzoyl Peroxide → 2-(Bromomethyl)-5-fluorobenzonitrile

Participants

Reaction Steps

A mixture of 5-fluoro-2-methylbenzonitrile (2.0 g, 0.015 mol), NBS (3.2 g, 0.018 mol) and benzoylperoxide (0.25 g) in carbontetrachloride (25.0 ml) was heated to reflux for 6 h, under argon atmosphere. The reaction mixture was cooled and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (5% EtOAc in hexane) to afford 2-(Bromomethyl)-5-fluorobenzonitrile (1.9 g, 60%) as a colorless liquid: 1H NMR (CDCl3/400 MHz) δ7.59 (m) 7.58 (m, 1H), 7.38 (m, 1H), and 7.25 (m, 1H).

Provenance & Evidence