HCID 57809808, compound → HCID 57809750, compound

Participants

Reaction Conditions

Reaction Steps

To a chilled (0° C.) suspension of Soxhlet-extraction-purified CuI (14.28 g, 0.075 mol, 1.5 equiv.) in 150 mL of anhydrous diethyl ether, was added a 1.6M solution of methyl lithium (84.4 mL, 0.135 mol, 2.7 equiv.) in diethyl ether. The mixture was stirred for 10 minutes, cooled to −25° C. and a solution of (Z)-3-(3-bromophenyl)-2-cyanobut-2-enoic acid methyl ester (14.13 g, 0.05 mol) in 150 mL of anhydrous diethyl ether was added dropwise. The mixture was stirred at −25° C. for 30 minutes, warmed to room temperature, and stirred overnight. The reaction was quenched with saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organics were washed with brine, dried with sodium sulfate, filtered, and concentrated in vacuo to afford a brown oil. The oil was purified via flash chromatography using a hexanes-ethyl acetate gradient to afford 3-(3-bromophenyl)-2-cyano-3-methylbutyric acid methyl ester. Yield: 8.88 g (60%).

Provenance & Evidence