Boron tribromide → (3,4-Dichlorophenyl)(4-hydroxyphenyl)methanone

HRID 1857192Notes

Reaction equation

HRID 1857192 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]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 27581233,4-Dichloro-4'-methoxybenzophenone

Product 1

HCID 12299673(3,4-Dichlorophenyl)(4-hydroxyphenyl)methanoneYield 77.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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%).

Workup

  1. temperaturewhile cooled in ice
  2. custompartitioned between water and chloroform
  3. dry with materialThe chloroform layer was dried with anhydrous magnesium sulfate
  4. customAfter removing the solvent
  5. distillationby reduced-pressure distillation
  6. customthe resulting residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate

Sources & evidence

ORD record
ord-7564e04b974649f3ae75ebd7718eaa92
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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