Phosphorus tribromide → 3-(Bromomethyl)-5-(trifluoromethyl)benzonitrile

Participants

Reaction Steps

A solution of 3-hydroxymethyl-5-trifluoromethyl-benzonitrile (100 mg, 0.497 mmol) in dichloromethane (1 ml) at 0° C. was treated in a dropwise manner with a solution of phosphorus tribromide (0.3 ml, 1M, 0.3 mmol) in dichloromethane at 0° C. for 1 hour. The ice bath was removed and the reaction was stirred at room temperature for 2 hours. Reaction was quenched with sat'd NaHCO3 solution until reaction was no longer yellow-orange in color. Reaction was extracted with dichloromethane and organic layer was dried over anhydrous magnesium sulphate and concentrated in vacuo. The crude residue was purified by chromatography on Biotage column (12+M), eluting with ethyl acetate in heptane 0-30% (10CV), 30% (2CV) to yield the title compound (56 mg, 43%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.46 (s, 2H) 7.80 (s, 1H) 7.84 (s, 2H).

Provenance & Evidence