Dimethylformamide → 4-Bromo-2-(trifluoromethoxy)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-(trifluoromethoxy)iodobenzene (25 g, 68 mmol) and zinc(II) cyanide (4.0 g, 34 mmol) in 150 mL of degassed dimethylformamide was added tetrakis(triphenylphosphine)palladium (3.1 g, 4 mole %). The solution was stirred at 80 ° C. for one hour, then cooled to room temperature. Additional portions of zinc(II) cyanide (800 mg) and tetrakis(triphenylphosphine)palladium (700 mg) were added, and the solution was heated at 80° C. for 3 hours. The mixture was diluted with EtOAc and extracted with saturated NaHCO3 solution and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. Purification by silica gel column chromatography (0-5% ether/hexane) gave the titled product.

Provenance & Evidence