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

HRID 1857133ノート

反応式

HRID 1857133 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 539663472,6-Dihydroxy-4-methylphenyl 4-hydroxyphenyl ketone収率 68%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-531b49b139a54b159537aa7d286eaf10
出典データセット
uspto-grants-2000_11
特許番号
US06143764

反応ノート

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