Boron tribromide → 4-Cyclohexyl-3-isopropyl-phenol
Reaction equation
[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]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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.
Workup
- customThe reaction mixture was then quenched with MeOH (5 mL)
- additionafter which aqueous sodium hydrogen carbonate (10 mL) was added
- stirringThe reaction mixture was stirred at room temperature for one hour
- extractionextracted with CH2Cl2 three times
- washThe organic phase was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-660d62a3883840528717127d539e9152
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642603B2
Reaction notes
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