Boron tribromide → 4,4'-Dihydroxybenzil

HRID 1620357

반응식

HRID 1620357 반응식
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

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 710434,4'-Dimethoxybenzil2회

생성물 1

HCID 4582044,4'-Dihydroxybenzil

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8f58a185f81d4038ba6863ed558e69ef
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08772443B2

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