Method for fluoromethylation of alcohols via halogenative decarboxylation

摘要

A method for fluoro-methylation of an alcohol comprising the steps of : reacting an alcohol of the formula R1C (CX3)2OH with an alpha-haloester of the formula X2CH2CO2R2 to form an alpha-alkoxy ester. Wherein R' is selected from the group consisting of hydrogen and alkyl groups; R2 is selected from the group consisting of hydrogen and alkyl groups; X, at each occurrence, is independently selected from the group consisting of hydrogen, bromine, fluorine, and chlorine; and X2 is selected from the group consisting of bromine and chlorine. The method comprises the steps of saponifying said alpha-alkoxy ester to form an alpha-alkoxy acid; heating at reflux said alpha-alkoxy acid with lead tetra acetate and a chlorinating agent to form a chloromethyl ether of the formula R'C(CX3) 2OCH2CI ; and converting said chloromethyl ether to a fluoride compound of the formula R'C (CX3)2OCH2F with a fluorinating agent.