Benzoyl Peroxide → 4-(Bromomethyl)-3-fluorobenzonitrile

Participants

Reaction Conditions

Reaction Steps

NBS (Aldrich, 3.02 g, 17 mmol) and benzoylperoxide (Aldrich, 0.37 g, 1.5 mmol) was added to a solution of 2-fluoro-4-cyanotoluene (compound 5-2, 2.08 g, 15 mmol) in CCl4. The reaction mixture was heated at 80° C. for 14 hours. After cooling down to ambient temperature, the mixture was diluted with ether (100 ml) and washed with aqueous Na2S3O3, and dried (MgSO4). Removal of solvent under vacuum led to a yellow oil which was purified by flash chromatography. The title compound 5-3 (1.4 g, 42%) was obtained, together with a by-product, 3-fluoro-4-(bromomethyl)benzonitrile (5-4) (1.0 g, 30%). For the title compound (5-3): 1H NMR (CDCl3): δ 4.46 (s, 2H), 7.35 (d, 1H, J=8.0 Hz), 7.42 (d, 1H, J=8.0 Hz), 7.52 (t, 1H, J=8.0 Hz). For the by-product (5-4): 1H NMR (CDCl3): δ 6.90 (s, 1H), 7.35 (d, 1H, J=8.0 Hz), 7.55 (d, 1H, J=8.0 Hz), 7.96 (t, 1H, J=8.0 Hz).

Provenance & Evidence