[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].ClC1C=CC(O[CH2:20][C:21]#[N:22])=CC=1.CC(C)([O-])C.[K+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:8][C:9]=1[CH2:20][C:21]#[N:22])([O-:3])=[O:2]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.
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