α-(p-Toluenesulfonyl)-4-fluorobenzylisonitrile

165806-94-0

165806-95-1

4-Fluorophenyl-toluenesulfonylmethylformamide (2.01 g, 6.25 mmol) was used as the raw material, which was dissolved in DME (32 mL) and cooled to -10 °C. POCl3 (1.52 mL, 16.3 mmol) and triethylamine (4.6 mL, 32.6 mmol, dissolved in DME 3 mL) were added sequentially while keeping the internal temperature below -5 °C. The reaction mixture was slowly warmed to room temperature over 1 h and subsequently poured into water and extracted with EtOAc. The organic phase was washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated. The residue was ground with petroleum ether and filtered to give α-tosyl(4-fluorobenzyl)isonitrile (1.7 g, 90% yield).1H NMR (CDCl3) δ 7.63 (d, 2H), 7.33 (m, 4H), 7.10 (t, 2H), 5.60 (s, 1H), 2.50 (s, 3H).