Hydrochloric Acid → 3-Hydroxy-2-(m-methylphenyl)-5-trifluoromethylbenzo[b]thiophene

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Reaction Conditions

Reaction Steps

To a slurry of sodium hydride (50% dispersion in mineral oil) (253 mg, 5.27 mmol) in N,N-dimethylformamide (3 ml) at 75° C. under a nitrogen atmosphere was added a solution of methyl 2-(m-methylbenzylthio)-5-trifluoromethylbenzoate (885 mg, 2.60 mmol) in N,N-dimethylformamide (12 ml). Gas evolution was observed during the 20 minute addition period. After stirring an additional 45 minutes at 75° C., water (70 ml) was added, and the aqueous mixture was brought to pH5-6 at room temperature with 2N hydrochloric acid. Extraction of the mixture with diethyl ether followed by washing the combined extracts with water and evaporation gave a residue that was chromatographed on a column of silica gel (Merck 7734, packed as a slurry in 15:1 hexane-ether). Elution with 15:1 hexane-ether containing 1% acetic acid and evaporation of the appropriate fractions afforded the product as a white crystalline solid; yield 450 mg (56%); m/z 308 (M+.); m.p. 124°-126°.

Provenance & Evidence