Potassium Carbonate → 3,4-Dimethoxy-2-(2,2,2,-trifluoroethoxy)benzonitrile

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Reaction Steps

Potassium carbonate (6.91 g, 0.05 mol) was added to a stirred solution of 2-hydroxy-3,4-dimethoxybenzonitrile (from Example 10(c), 5.61 g, 0.031 mol) in dimethylformamide (30 ml). This was followed by the addition of a solution of 2,2,2-trifluoroethyl triflate (23.2 g, 0.10 mol) in dichloromethane (100 ml) and the reaction was stirred at room temperature for 18 hours. The reaction was partitioned between 2N hydrochloric acid and ethyl acetate, the organic layer separated, washed sequentially with saturated aqueous brine and water, dried (MgSO4) and evaporated under reduced pressure. Trituration with diethyl ether followed by filtration afforded the subtitle compound as a colourless solid (7.67 g, 94%). Rf 0.76 (dichloromethane:methanol 95:5, v/v). MS m/z 279 (MNH4)+

Provenance & Evidence