P-Nitrobenzotrifluoride → (2-Nitro-5-trifluoromethylphenyl) acetonitrile

Participants

Reaction Conditions

Reaction Steps

4-Nitrobenzotrifluoride (5 g, 0.026 mole) and 4-chlorophenoxyacetonitrile (4.86 g, 0.029 mole) in dry DMF (50 ml) were added dropwise to a solution of potassium-t-butoxide (6.4 g, 0.057 mole) in dry DMF (30 ml) under argon at −10° C. over 1 hour. The mixture was stirred at −10° C. for a further 3 hours, after which it was poured into 5N HCl/ice water (1:1) (300 ml) and extracted into DCM (3×200 ml). The DCM extract was washed with 10% aqueous sodium hydroxide solution, 5N hydrochloric acid and brine, dried (Na2SO4) and evaporated in vacuo. The resulting oil was chromatographed on silica gel eluting with 20% ethyl acetate/60-80° petroleum ether to afford the title compound (1.9 g, 32%) as an orange oil.

Provenance & Evidence