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Abstract
A convenient method is reported for the synthesis of the biologically important intermediate, 3,5-bis(trifluoromethyl)-salicylic acid, by a sequence involving diazotization/iodination of 2-bromo-3,5-bis(trifluoromethyl)aniline, displacement of the bromide with sodium methoxide, and carboxylation of the anion generated by lithium-iodine exchange with carbon dioxide. Alternatively, the anion could be carbonylated with dimethylformamide and the resulting aldehyde oxidized with Jones reagent. Demethylation of 3,5-bis(trifluoromethyl)anisic acid with boron tribromide gave the title compound.
Notes
Fed. Reg., Oct. 30, 1975, 40, 50527.
Compound 11 was prepared by the following reactions: