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

HRID 1857133Notes

Reaction equation

HRID 1857133 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[C:16]([O:17]C)=[CH:15][C:14]([CH3:19])=[CH:13][C:12]=2[O:20]C)=[O:10])=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[C:16]([OH:17])=[CH:15][C:14]([CH3:19])=[CH:13][C:12]=2[OH:20])=[O:10])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 542550422,6-Dimethoxy-4-methylphenyl 4-methoxyphenyl ketone

Product 1

HCID 539663472,6-Dihydroxy-4-methylphenyl 4-hydroxyphenyl ketoneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  1. temperaturewhile cooled in ice
  2. custompartitioned with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was removed by 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-531b49b139a54b159537aa7d286eaf10
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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