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

HRID 237819ノート

反応式

HRID 237819 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 685276534-Cyclohexyl-3-isopropyl-phenol収率 120.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-660d62a3883840528717127d539e9152
出典データセット
uspto-grants-2014_02
特許番号
US08642603B2

反応ノート

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