New routes to diethyl 1-fluoromethylphosphonocarboxylates and diethyl 1-fluoromethylphosphonocarboxylic acid

Article abstract of DOI:10.1016/S0040-4020(97)00312-8

Diethyl 1-fluoromethylphosphonocarboxylic esters 4, bearing a variety of ester groups (alkyl, aryl), have been conveniently prepared in a one-pot process, by reaction of chloroformates with 1-lithio-1-fluoro-1-(trimethylsilyl)methylposphonate 2 derived from 1,1-dibromo-1-fluoromethylphosphonate 1. The overall yields generally range from 80 to 91%. Reaction of 2 with CO₂ leads to a novel efficient synthesis of diethyl 1-fluoromethylphosphonocarboxylic acid 7 in 86% yield.