2,2,2-Trifluoroacetaldehyde O-(Aryl)oxime: A Precursor of Trifluoroacetonitrile

The preparation of 2,2,2-trifluoroacetaldehyde O-(aryl)oxime, a previously inaccessible precursor of trifluoroacetonitrile, via reaction of hydroxylamine and trifluoroacetaldehyde hydrate is reported. This precursor released CF3CN in quantitative yield under mildly basic conditions. The precursor was successfully used in the synthesis of trifluoromethylated oxadiazoles. The facile, cost-effective, scalable, and recyclable procedure makes these trifluoroacetonitrile precursors generally applicable.

Automated summary

This study reports the preparation of 2,2,2-trifluoroacetaldehyde O-(aryl)oxime, an inaccessible precursor of trifluoroacetonitrile, through the reaction of hydroxylamine and trifluoroacetaldehyde hydrate. Under mildly basic conditions, this precursor releases CF3CN with quantitative yield. It has been successfully utilized in the synthesis of trifluoromethylated oxadiazoles. The facile, cost-effective, scalable, and recyclable procedure of these trifluoroacetonitrile precursors makes them generally applicable.