Ethyl Acetate → HCID 21711561, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromobenzonitrile (500 mg, 2.75 mmol) and S-(−)-α-phenylethylalcohol (403 mg, 3.30 mmol) in toluene (5 mL) were added sodium hydride (220 mg, 5.49 mmol; 60% in oil), tris(dibenzylideneacetone)dipalladium(0) (38 mg, 0.0413 mmol) and 2,2-bis(di-p-tolylphosphino)-1,1-binaphthyl (67 mg, 0.099 mmol), and the solution was stirred at 70° C. for 4 hours. The reaction solution was allowed to room temperature, ethyl acetate and water were added for partitioning, the organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was purified by silica gel column chromatography (hexane:ethyl acetate), and 4-(1-phenyl-ethoxy)-benzonitrile (159 mg, 26%) was obtained as a colorless oil.

Provenance & Evidence