Boron tribromide → 2,6-Dihydroxy-4-methylphenyl 4-hydroxyphenyl ketone

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Reaction Steps

2,6-Dimethoxy-4-methylphenyl 4-methoxyphenyl ketone (321 mg) obtained in Example 45 was dissolved in anhydrous methylene chloride (10 ml), commercially available boron tribromide (349 ml) was added slowly while cooled in ice, and the admixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and then partitioned with ethyl acetate. The ethyl acetate layer was washed with brine and then dried with anhydrous magnesium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to obtain 87 mg of the title compound (yield: 68%).

Provenance & Evidence