Abbott Laboratories Corporation

Christopher Behme

Christopher Bieniarz

Kornepati V Ramakrishna

A method for fluoromethylation of an alcohol via halogenative decarboxylation. The method includes the step of reacting an alcohol of the formula R,C(CX,),OH with an alpha-haloester of the formula X,CH,CO,R,to form an alpha-alkoxy ester, wherein R,is selected from the group consisting of hydrogen and alkyl groups, wherein R,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 X,is selected from the group consisting of bromine and chlorine. The resulting alpha-alkoxy ester is saponified to form an alpha-alkoxy acid which is heated at reflux with lead tetraacetate and a chlorinating agent to form a chloride compound of the formula R,C(CX,),OCH,Cl. The chloride compound is converted to a fluoride compound of the formula R,C(CX,),OCH,F with a fluorinating agent.

Method for fluoromethylation of alcohols via halogenative decarboxylation

A method for synthesizing fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether. The method includes the step of combining in the presence of aluminum trichloride a quantity of hexafluoroisopropanol and a quantity of either 1,3,5-trioxane or paraformaldehyde to produce sevochlorane. The resulting sevochlorane is then combined with an alkali metal fluoride to produce fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether.

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Christopher Behme