Sodium Carbonate → 3-Benzylbenzonitrile

Participants

Reaction Steps

A mixture of benzeneboronic acid (2.05 g, 16.8 mmol), 3-bromomethylbenzonitrile (3 g, 15.3 mmol), dichlorobis(triphenylphosphine)palladium(II) (1.07 g, 1.53 mmol), tri-o-tolylphosphine (0.465 g, 29 mmol) and sodium carbonate (3.08 g, 29 mmol) in aqueous acetonitrile (1:10, 220 mL) was refluxed under nitrogen for 2 hours, cooled to room temperature, concentrated under reduced pressure, taken up in dilute hydrochloric acid (2N, 150 mL) and extracted with diethyl ether (3×70 mL). The organic extracts were combined, washed with water (2×100 mL), saturated aqueous sodium bicarbonate (100 mL), brine (70 mL), and dried over magnesium sulfate, then adsorbed on silica and chromatographed on silica using a mobile phase of ethyl acetate/hexane. The major fraction was concentrated under reduced pressure to leave a colorless liquid. Yield 2.1 g (71 percent). 1H NMR (CDCl3) δ 7.49 (dt, J1=7.5 Hz, J2=1.2 Hz, 1H), 7.46 (br, 1H), 7.43 (dt, J1=7.8 Hz, J2=1.8 Hz, 1H), 7.39 (d, J=7.5 Hz, 1H), 7.33 (dt, J1=6.9 Hz, J2=2.1 Hz, 1H), 7.30 (dt, J1=7.2 Hz, J2=1.2 Hz, 1H), 7.25 (dt, J1=7.2 Hz, J2=1.5 Hz, 1H), 7.15 (dt, J1=6.9 Hz, J2=1.8 Hz, 2H), 4.01 (s, 2H); EI/MS 193 m/e (M+); CI/MS 194 m/e (M+1);

Provenance & Evidence