Boron tribromide → 4-Cyclohexyl-3-isopropyl-phenol

HRID 237819노트

반응식

HRID 237819 반응식
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][C:8]=2[CH:15]([CH3:17])[CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[CH:15]([CH3:17])[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

4

반응물 2

HCID 25134Boron tribromideHCID 68529356Cyclohexyl-4-methoxy-2-isopropyl-benzene

생성물 1

HCID 685276534-Cyclohexyl-3-isopropyl-phenol수율 120.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To 1-cyclohexyl-4-methoxy-2-isopropyl-benzene (2.09 g, 9.0 mmol) in CH2Cl2 (20 mL) was added BBr3 (1 M in CH2Cl2, 22.5 mmol) dropwise at 0° C. This mixture was stirred at 0° C. for two hours. The reaction mixture was then quenched with MeOH (5 mL), after which aqueous sodium hydrogen carbonate (10 mL) was added. The reaction mixture was stirred at room temperature for one hour and extracted with CH2Cl2 three times. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (0-2% EtOAc/heptane) provided 2.36 g of the title compound.

후처리

  1. customThe reaction mixture was then quenched with MeOH (5 mL)
  2. additionafter which aqueous sodium hydrogen carbonate (10 mL) was added
  3. stirringThe reaction mixture was stirred at room temperature for one hour
  4. extractionextracted with CH2Cl2 three times
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-660d62a3883840528717127d539e9152
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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