Acetonitrile → (2Z)-3-Amino-3-[4-(trifluoromethyl)phenyl]prop-2-enenitrile

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Reaction Steps

28.1 g (278 mmol) of diisopropylamine are introduced into 450 ml of THF at −70° C. in a three-neck flask with mechanical stirrer under argon. 148 ml of N-butyllithium solution (1.6 M in hexane, 237 mmol) are added dropwise at such a rate that the temperature does not rise above −60° C. The mixture is stirred for 10 min and then a solution of 12.9 ml (245 mmol) of acetonitrile in 100 ml of THF is slowly added dropwise, and the suspension is stirred for 30 min. Then a solution of 28 g (164 mmol) of 4-(trifluoromethyl)benzonitrile in 100 ml of THF is added dropwise, and the mixture is stirred at −70° C. for 20 min. It is allowed to reach RT slowly and is stirred at RT for a further 16 h. 150 ml of water are added, most of the THF is distilled off, and water and dichloromethane are added. The organic phase is washed with saturated aqueous sodium chloride solution. Removal of the solvent results in dark crystals which are purified by stirring with diisopropyl ether (40 ml once, 20 ml twice). The crystals are filtered off, washed with petroleum ether and dried. 27 g (78% of theory) of the product are obtained as a solid.

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