Gram-Scale Preparation of 4,4,4-Trifluorobut-2-ynal from HFO-1234yf

Abstract

A synthetic protocol has been developed for the gram-scale synthesis of 4,4,4-trifluorobut-2-ynal based on the commercially available, environmentally friendly fourth-generation refrigerant HFO-1234yf (2,3,3,3-tetrafluoropropene). The synthesis comprises the three following stages: obtaining 3,3,3-trifluoropropyne, its transformation into 4,4-diethoxy-1,1,1-trifluorobut-2-yne via the Bodroux–Chichibabin reaction, and subsequent hydrolysis of the latter compound, giving the final 4,4,4-trifluorobut-2-ynal. The proposed protocol expands the synthetic potential of CF3-alkynes by providing preparative availability for an original organofluorine substance.