A solution was prepared by dissolving 4-bromophenylacetonitrile (10.0 g, 51.0 mmol) in tetrahydrofuran (200 mL) at room temperature. Subsequently, the solution was slowly added dropwise to a suspension of sodium hydride (60% mineral oil dispersion, 6.0 g, 153 mmol) in tetrahydrofuran (400 mL) for 30 min. Upon completion of the dropwise addition, iodomethane (7.6 mL, 122 mmol) was slowly added over a period of 30 min, during which time a water bath was occasionally used to cool the reaction to maintain the reaction temperature below 40 °C. The reaction mixture was stirred at room temperature. The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the mixture was poured into water (500 mL) and extracted with ethyl acetate (2 x 300 mL). The organic layers were combined, washed sequentially with brine (2 x 300 mL), dried over anhydrous magnesium sulfate, filtered and the solvent was concentrated. The crude product was purified by silica gel column chromatography using hexane solution containing 2% ethyl acetate as eluent to afford 2-(4-bromophenyl)-2-methylpropionitrile (11 g, 96% yield) as a yellow oil.1H NMR (300 MHz, CDCl3) δ ppm: 1.7 (s, 6H), 7.35 (dd, 2H), 7.53 (dd, 2H).
