Synthesis of 1,1,1-trichloro[fluoro]-3-alken-2-ones using ionic liquids

The synthesis of a series of ten 1,1,1-trichloro[fluoro]-3-alken-2-ones [CX3C(O)C(R2)C(R1)OR, where X = Cl and F; R1/R2/R = H/H/Et, Me/H/Me, H/Me/Et, H/(CH2)2 and H/(CH2)3] from the acylation reactions of enol ethers with trichloroacetyl chloride or trifluoroacetic anhydride in the presence of equimolar amounts of pyridine and 10% mol-equiv. of imidazolium based ionic liquid [BMIM]·BF4 or [BMIM]·PF6 is reported. The reaction time, the ionic liquid recyclation and yields were investigated and this method showed advantages over the methods described in the literature.

Graphical abstracti: Pyridine (1 equiv.), [BMIM]·BF4 or [BMIM]·PF6 (0.1 equiv.), 0° to r.t., 1.5 h. Figure optionsDownload full-size imageDownload as PowerPoint slide