190 mg (1.0 mmol) of 2-trifluoromethylbenzoic acid, 178 mg (0.83 mmol) of 2-(3,3-dimethyl-but-1-ynyl)phenylamine, 215 mg (1.67 mmol) of N,N-diisopropylethylamine and 583 mg (1.25 mmol) of PyBrOP in 8 ml of acetonitrile were stirred at room temperature for 4 days. 10 ml of ethyl acetate/water 1:1 were added to the mixture and the organic phase was separated off and washed with 10 ml of saturated ammonium chloride solution and subsequently with 10 ml of water. Separation, concentration and drying of the organic phase gave 950 mg of crude product. Column-chromatographic purification on silica gel 60 (petroleum ether/ethyl acetate 10:1→ethyl acetate) gave 110 mg of N-[2-(3,3-dimethylbut-1-ynyl)phenyl]-2-trifluoromethylbenzamide [logP (pH 2.3)=4.55].
