Boron tribromide → 4,4'-Dihydroxybenzil

HRID 1620357

反応式

HRID 1620357 の反応式
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:20])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18]C)=[CH:14][CH:13]=2)=[O:11])=[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](=[O:20])[C:10]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[O:11])=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 25134Boron tribromideHCID 710434,4'-Dimethoxybenzil2 回

生成物 1

HCID 4582044,4'-Dihydroxybenzil

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

1,2-bis(4-methoxyphenyl)ethane-1,2-dione (5 g, 18.52 mmol) was dissolved in CH2Cl2 and cooled to −78° C. (solid occurred again). BBr3 (8.3 m, 87.82 mmol) was added and mixture was allowed to warm to room temperature and stirred for 15 hrs. TLC check showed 1,2-bis(4-methoxyphenyl)ethane-1,2-dione completely disappeared. The reaction mixture was poured into ice, extracted by EtOAc, washed with NaCl solution, dried over MgSO4. The solvent was removed by vacuum, and the residue was purified by column chromatography to give compound 5, 1,2-bis(4-hydroxyphenyl)ethane-1,2-dione, as confirmed by the following nuclear magnetic resonance (NMR) data obtained therefrom: 1H NMR (500 MHz, DMSO): δ 10.8 (s, 2H), 7.71 (d, J=8.8 MHz, 4H), 6.90 (d, J=8.8 MHz, 4H) ppm.

後処理

  1. temperatureto warm to room temperature
  2. additionThe reaction mixture was poured into ice
  3. extractionextracted by EtOAc
  4. washwashed with NaCl solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed by vacuum
  7. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-8f58a185f81d4038ba6863ed558e69ef
出典データセット
uspto-grants-2014_07
特許番号
US08772443B2

関連ノート

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