Acetonitrile → 3-(4-Fluoro-2-methylphenyl)-3-oxopropanenitrile

Participants

Reaction Conditions

Reaction Steps

To a suspension of hexane-washed sodium hydride (60% oil dispersion, 995 mg, 24.9 mmol) was added dropwise a THF solution (20 mL) of methyl 4-fluoro-2-methylbenzoate (3.8 g, 22.6 mmol) and anhydrous acetonitrile (2.4 mL, 45.2 mmol). The mixture was stirred at 70° C. for 16 h, and then cooled to rt. The resulting mixture was diluted with ethyl acetate (20 mL) and 1 N HCl (10 mL) and the layers were partitioned. The organic phase was washed with water (3×20 mL) and brine (20 mL), dried (Na2SO4), and concentrated under reduced pressure to afford 4.0 g of yellow oil, which was taken to the next step without further purification. ES-MS m/z 178.2 (MH+); HPLC RT (min) 2.22.

Provenance & Evidence