Azobisisobutyronitrile → 2-(Bromomethyl)-4-(trifluoromethoxy)benzonitrile

Participants

Reaction Steps

To a solution of 2-methyl-4-trifluoromethoxy-benzonitrile 15 (1.3 g, 6.5 mmol) in carbon tetrachloride (25 mL) was added N-bromosuccinimide (1.7 g, 9.7 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield a clear oil (70%). 1H NMR (400 MHz,CDCl3) δ7.73 (d, J=8.4 Hz, 1 H, Ar), 7.41 (s, 1 H, Ar), 7.27 (d, J=8.4 Hz, 19 H, Ar), 4.61 (s, 2 H, CH2).

Provenance & Evidence