Boron tribromide → Methyl 3-(3-hydroxyphenyl)benzoate

HRID 1069077ノート

反応式

HRID 1069077 の反応式
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[CH3:15][O:14][C:12]([C:11]1[CH:10]=[C:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([OH:2])[CH:4]=2)[CH:18]=[CH:17][CH:16]=1)=[O:13]

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 5152373Methyl 3'-methoxy[1,1'-biphenyl]-3-carboxylate

生成物 1

HCID 5097338Methyl 3-(3-hydroxyphenyl)benzoate収率 55.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

To a −78° C. solution of methyl 3-(3-methoxyphenyl)-benzoate (1.48 g) in anhydrous methylene chloride (16 mL) was added dropwise a solution of boron tribromide in methylene chloride (1.0 M, 16.3 mL). The mixture was stirred at −78° C. for 30 min, allowed to warm to 0° C., and stirred for 2 h. The mixture was quenched by addition of saturated aqueous sodium bicarbonate (50 mL), and diluted with methylene chloride (50 mL). The mixture was placed in a separatory funnel, and the organic layer was separated, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel chromatography (eluting with 5:1 hexanes/ethyl acetate) afforded the title compound (769 mg) as a pale yellow oil.

後処理

  1. temperatureto warm to 0° C.
  2. stirringstirred for 2 h
  3. customThe mixture was quenched by addition of saturated aqueous sodium bicarbonate (50 mL)
  4. additiondiluted with methylene chloride (50 mL)
  5. customThe mixture was placed in a separatory funnel
  6. customthe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give the crude product
  11. customPurification
  12. washby silica gel chromatography (eluting with 5:1 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-a830c2bd6c4b40c98a5ea2878bb4ab03
出典データセット
uspto-grants-2001_06
特許番号
US06251925B1

反応ノート

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