Boron tribromide → (4-Hydroxyphenyl)(4-iodophenyl)methanone

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Reaction Steps

4-Methoxyphenyl 4-iodophenyl ketone (722 mg) obtained in Example 176 was dissolved in dichloromethane (20 ml), a solution of 1.0 M boron tribromide in dichloromethane (9 ml) was added while cooled in ice, and the admixture was stirred at room temperature overnight. The reaction mixture was then poured into ice water and partitioned between water and chloroform. The chloroform layer was dried with anhydrous magnesium sulfate and the solvent was removed by reduced-pressure distillation. The resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to obtain 380 mg of the title compound (yield: 55%).

Provenance & Evidence