Potassium Hydroxide → 3-[(4-Fluorophenyl)thio]-2-hydroxy-2-methylpropanoic acid

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Reaction Steps

The methyl 2-methyl-oxirane-carboxylate of formula (1), which was obtained by epoxidation, was reacted with 4-fluorothiophenol [formula (2)] in the presence of sodium hydride under the conditions listed in Scheme-2. The obtained methyl 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionate of formula (3) was hydrolyzed with potassium hydroxide in aqueous ethanol over a period of 22 hours to yield the 2-hydroxy-2-methyl-3-(4-fluorophenylthio)-propionic acid of formula (4), which was converted into the acid chloride of formula (5) with thionyl chloride in dimethyl acetamide at −15° C.

Provenance & Evidence