Water → 2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile

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Reaction Steps

A solution of 5-amino-4-(p-chlorophenyl)-2-(trifluoromethyl)oxazole, triflate salt (16.5 g, 0.04 mol) in dimethylformamide is treated at 10° C. with 2-chloroacrylonitrile (5.25 g, 0.06 mol) under a nitrogen atmosphere, warmed to room temperature, held at room temperature for 4 hours, and treated with a mixture of ethyl acetate and water. The phases are separated and the organic phase is washed with water and concentrated to give a wet solid residue. Flash column chromatography on silica gel, packed with 15% ethyl acetate in heptane and eluted with 20% ethyl acetate in heptane of the residue gives, on crystallization from ethyl acetate/heptane, the title product as a pale yellow solid, 7.1 g (65% yield), mp 238.0°-241.0° C., identified by NMR analysis.

Provenance & Evidence