N-bromobutanimide → 4-(bromomethyl)-3-(trifluoromethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-methyl-3-trifluoromethyl-benzonitrile (370 mg, 2 mmol), N-Bromosuccinimide (356 mg, 2 mmol) and benzoyl peroxide (15 mg) in CCl4 (8 mL) was stirred at 85° C. for 16 hrs. The reaction mixture was then partitioned between saturated aqueous NaHCO3 and DCM. DCM layer was dried over Na2SO4, filtered, and the solvent evaporated in vacuo to yield a crude solid which was purified via flash chromatography (15% EtOAc in n-heptane) to yield the title compound as a solid (460 mg, 85%).

Provenance & Evidence