Anhydrous tetrahydrofuran solution (30 mL) of 2-(3-nitrophenyl)acetonitrile (4.2 g, 25.9 mmol) was added slowly and dropwise to an anhydrous tetrahydrofuran (30 mL) suspension of 50% sodium hydride (6.84 g, 171 mmol) cooled in an ice bath. After dropwise addition, stirring was continued for 30 min, followed by slow addition of iodomethane (12.63 mL, 202 mmol). The reaction mixture was gradually warmed to room temperature and stirred overnight. After completion of the reaction, the reaction was quenched with ice water. The reaction mixture was extracted with ethyl acetate, the organic layer was separated, washed with water and dried over anhydrous sodium sulfate. The crude product was obtained by filtration and concentration. The crude product was purified by silica gel column chromatography using ethyl acetate/hexane (5:95) as eluent to afford 2-methyl-2-(3-nitrophenyl)propionitrile (2.1 g).1H NMR (400 MHz, CDCl3) δ 8.33-8.32 (m, 1H), 8.24-8.21 (m, 1H), 7.92-7.89 (m, 1H), 7.63 (t, J = 8.00 Hz, 1H), 1.82 (s, 6H).GCMS: 190.11 [M+].
