Water → HCID 19073539, compound

Participants

Reaction Conditions

Reaction Steps

A solution of N-(p-chloro-α-cyanobenzyl)-2,2,2-tri-fluoro-N-isopropylacetamide (6.1 g, 0.02 mol) in toluene is treated at room temperature with tetrafluoroboric acid diethyl etherate (4.2 g as is, 3.6 g real, 0.022 mol) under a nitrogen atmosphere, heated to 60° C., treated with 2-chloroacrylonitrile (2.62 g, 0.03 mol) over 15-20 minutes, held at 60° C. for 3 hours, cooled to room temperature and treated with ethyl acetate and water. The phases are separated and the organic phase is washed with water and concentrated to give a brown gum residue. Flash column chromatography of the residue on silica gel packed and eluted with 15% ethyl acetate in heptane gives the title product as a brown oil, 1.3 g (20.8% yield), identified by 1H and 19F NMR and mass spectral analyses.

Provenance & Evidence