Boron tribromide → (3,4-Dichlorophenyl)(4-hydroxyphenyl)methanone
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[C:13]([Cl:18])[CH:12]=2)=[O:10])=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
3,4-Dichlorophenyl 4-methoxyphenyl ketone (235 mg) obtained in Example 120 was dissolved in dichloromethane (2 ml), a solution of 1.0 M boron tribromide in dichloromethane (7 ml) was added while cooled in ice, and the admixture was stirred at room temperature for two days. The reaction mixture was then poured into ice water and partitioned between water and chloroform. The chloroform layer was dried with anhydrous magnesium sulfate. After removing the solvent by reduced-pressure distillation, the resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate to obtain 173 mg of the title compound (yield: 77%).