Method for fluoromethylation of alcohols via halogenative decarboxylation

A method for fluoromethylation of an alcohol comprising 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 Ri is selected from the group consisting of hydrogen and alkyl groups, wherein R2 is selected from the group consisting of hydrogen and alkyl groups, wherein X, at each occurrence, is independently selected from the group consisting of hydrogen, bromine, fluorine, and chlorine, and wherein X2 is selected from the group consisting of bromine and chlorine, wherein said step of reacting is conducted in the presence of a solvent and wherein said solvent is selected from the group consisting of an ether and tetrahydrofuran;
• saponifying said alpha-alkoxy ester to form an alpha-alkoxy acid;
• heating at reflux said alpha-alkoxy acid with lead tetraacetate and a chlorinating agent to form a chloromethyl ether of the formula R1C(CX3)2OCH2Cl;
• and
• converting said chloromethyl ether to a fluoride compound of the formula R1C(CX3)2OCH2F with a fluorinating agent.