Potassium Acetate → 3'-Bromo-4'-acetoxymethyl-1,1'-biphenyl-2-nitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of 662 mg (1.89 mmol) of 3'-bromo-4'-bromomethyl-1,1'-biphenyl-2-nitrile (Step D) in 10 mL of dry dimethyl formamide was added 925 mg (9.43 mmol) of potassium acetate. The reaction mixture was heated at 50° C. for 2 hours then diluted with 100 mL of water. The mixture was extracted with ethyl acetate (3×100 mL). The organic extracts were combined, washed with water (100 mL), saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL). The solution was dried over magnesium sulfate, filtered and the solvent removed under vacuum to give an oil which was purified by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (75:25), to afford 400 mg (64%) of the product as a white solid. 1H NMR (200 MHz, CDCl3): δ 2.14 (s, 3H), 5.22 (s, 2H), 7.4-7.8 (m, 7H). EI-MS: calculated for C16H12BrNO2 329; found 329, 331 (M+, 7%); 270, 272 (M-Br, 100%).

Provenance & Evidence