N-bromobutanimide → 4-(Bromomethyl)-3-fluorobenzonitrile

Participants

Reaction Steps

To a solution of 3-fluoro-4-methylbenzonitrile (5.0 g, 0.23 mol) in 100 mL of carbon tetrachloride was added N-bromosuccinimide (4.97 g, 0.28 mol) and AIBN (100 mg, 0.61 mmol) and the mixture was refluxed for six hours. The reaction was cooled and filtered. The filtrate was washed with water, dried over magnesium sulfate, filtered and the solvents were removed under vacuum to afford 5.44 g of the title compound as an off-white solid. 1H NMR indicated the presence of 20% starting material. 1H NMR (400 MHz, CDCl3) for the title compound: δ 7.54-7.30 (m, 3H), 4.83 (s, 2H).

Provenance & Evidence