5-Chloro-2-fluorophenylacetonitrile → Ammonia

Participants

Reaction Steps

Sodium borohydride (1.73 g, 45.51 mmol) was added portionwise to a solution of 5-chloro-2-fluorophenylacetonitrile (1.04 g, 6.15 mmol) and cobalt (II) chloride hexahydrate (2.18 g, 9.22 mmol) in methanol (30 mL) and the mixture was stirred at room temperature for 3 hours. The suspension was then filtered though Celite®, concentrated in vacuo and the residue was partitioned between 1M hydrochloric acid (40 mL) and dichloromethane (40 mL). The aqueous phase was separated, basified to pH 11 with 1M ammonia solution and extracted with dichloromethane (2×40 mL). The combined organic solution was washed with brine (30 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 100:0:0 to 98:2:0.2, to afford the title compound as a yellow oil in 33% yield, 350 mg. 1H NMR (400 MHz, CDCl3) δ: 7.28 (1H, m), 7.22 (1H, m), 7.05 (1H, m), 2.85 (2H, m), 2.77 (2H, m) ppm; LRMS APCI m/z 174 [M+H]+

Provenance & Evidence