Boron tribromide → 5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol

HRID 237762노트

반응식

HRID 237762 반응식
C[O:2][C:3]1[CH:15]=[C:14]2[C:6]([CH:7]3[CH:12]([CH2:13]2)[CH2:11][CH2:10][CH2:9][CH2:8]3)=[CH:5][CH:4]=1.B(Br)(Br)Br>C(Cl)Cl>[CH:15]1[C:14]2[CH2:13][CH:12]3[CH:7]([CH2:8][CH2:9][CH2:10][CH2:11]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:2]

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 685247797-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene

생성물 1

HCID 685276645,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol수율 81.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To 7-methoxy-2,3,4,4a,9,9a-hexahydro-1H-fluorene (1.95 g, 9.65 mmol) in CH2Cl2 (20 mL) was added BBr3 (1M in CH2Cl2, 24 mmol) dropwise at 0° C. This mixture was stirred at 0° C. for one hour. The reaction mixture was then quenched with MeOH (5 mL). Aqueous sodium hydrogen carbonate (10 mL) was added. The reaction mixture was stirred at room temperature overnight. The reaction mixture was extracted with CH2Cl2. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (EtOAc/heptane) provided 1.48 g of 5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ol.

후처리

  1. customThe reaction mixture was then quenched with MeOH (5 mL)
  2. additionAqueous sodium hydrogen carbonate (10 mL) was added
  3. stirringThe reaction mixture was stirred at room temperature overnight
  4. extractionThe reaction mixture was extracted with CH2Cl2
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4f2b34b4d6364c17a2c519c7d3a8a763
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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