A new preparative method for the synthesis of diethyl 1-diazo-2,2,2-trifluoroethylphosphonate via an imino phosphonate

Abstract

A preparative method for the synthesis of diethyl 1-diazo-2,2,2-trifluoroethylphosphonate from trifluoroacetic anhydride and benzyl carbamate via diethyl 1-benzyloxycarbonylimino-2,2,2-trifluoroethylphosphonate is developed. Optimum conditions for the chlorination of benzyl N-trifluoroacetylcarbamate with SOCl2—Py to afford the imidoyl chloride, phosphorylation of the latter under the conditions of the Arbuzov reaction, as well as diazotization of amino phosphonate with isopropyl nitrite are found.