Methyl iodide → 2-(3,4-Dichlorophenyl)propanenitrile

Participants

Reaction Conditions

Reaction Steps

To a −78° C. solution of (3,4-dichloro-phenyl)-acetonitrile (5.0 g, 26.9 mmol) in THF (60 mL) was added LHMDS (1 M in THF, 28.2 mL, 28.2 mmol). The reddish orange solution was stirred at −78° C. for 1 h and MeI (1.76 mL, 28.2 mmol) was added. The mixture was allowed to warm to rt overnight. The mixture was diluted with 1 M HCl (20 mL) and extracted with Et2O (3×). The combined organic layers were dried (MgSO4) and concentrated to provide a dark brown oil. The crude product was purified by flash chromatography (hexanes/EtOAc) to provide a colorless oil (5.0 g, 93%). 1H NMR (400 MHz, CDCl3): 7.52-7.42 (m, 2H), 7.25-7.18 (m, 1H), 3.88 (q, J=7.3, 1H), 1.64 (d, J=7.3, 3H).

Provenance & Evidence