To a 90% ethanol (500 mL) solution of 4-(bromomethyl)-1-chloro-2-methoxybenzene (68.5 g, 0.290 mol) was added sodium cyanide (28.5 g, 0.580 mol). The reaction mixture was stirred at 60 °C overnight. Upon completion of the reaction, the ethanol was removed by evaporation under reduced pressure and the residue was dissolved in water. The aqueous phase was extracted with ethyl acetate (300 mL × 3). The organic layers were combined, washed with saturated saline, and dried over anhydrous sodium sulfate. Purification by silica gel column chromatography (eluent: petroleum ether/ethyl acetate = 30:1) afforded 4-chloro-3-methoxyphenylacetonitrile (25 g, 48% yield).1H NMR (400 MHz, CDCl3) δ 7.36 (d, J = 8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H ).13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5.
