Carbon tetrabromide → alpha-Bromo-o-fluorotoluene

Participants

Reaction Steps

To a solution of (2-fluorophenyl)methanol (Aldrich, 10.0 g, 79.3 mmol) and triphenylphosphine (29.1 g, 111 mmol) in DCM was added CBr4 (31.6 g, 95.2 mmol) in small portions at 0° C. The mixture was stirred for 2 h at room temperature. The solvent was evaporated and the residue purified via flash chromatography (cyclohexanes:ethyl acetate 95:5) to give the title compound (14 g, 93%). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.42 (t, 1H), 7.36-7.28 (m, 1H), 7.17-7.07 (m, 2H), 4.55 (s, 2H).

Provenance & Evidence