Water → 4-Hydroxy-3,5-dimethoxybenzyl 4-hydroxyphenyl thioether

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Reaction Conditions

Reaction Steps

3,4,5-Trimethoxybenzyl 4-hydroxyphenyl thioether (3 g, 9.8 mmol), prepared as described in Example 1, was dissolved in 60 ml of dry methylene chloride, and cooled to -78° C. A solution of borontribromide (2.8 ml, 29.5 mmol) in 10 ml of methylene chloride was added dropwise to the above solution. The mixture was stirred to room temperature, and immediately cooled to 0° C. Water (50 ml) was then added dropwise, and the methylene chloride layer was separated. The crude product, obtained after being dried over magnesium sulfate and concentrated, was purified on silica gel column chromatography (ethyl acetate/n-hexane=1/2) to give 1.8 g (63% yield) of 4-hydroxy-3,5-dimethoxybenzyl 4-hydroxyphenyl thioether as a white solid.

Provenance & Evidence