Cyclohexyl bromide → Cyclohexylbenzene
Reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(CCN(C)C)C.Br[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.[Cl-].[NH4+]>>[CH:1]1([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Procedure
A mixture of phenyl magnesium bromide (1.25 mL of 0.96-M THF solution, 1.2 mmol) and TMEDA (181.1 μL, 1.2 mmol) was added to a mixture of bromocyclohexane (163.1 mg, 1.0 mmol) and FeCl3 (0.5 mL of 0.1-M THF solution, 5 mol %) at 0° C. over 20 minutes using an injection pump. After the addition of the mixture of Grignard reagent and TMEDA was completed, the reaction mixture was stirred at the temperature for 10 minutes. After treating with saturated aqueous ammonium chloride solution in a conventional manner, the reaction mixture was filtered through a pad of Florisil® and concentrated in vacuum. Using the internal standard (tetrachloroethane, 79 mg, 0.47 mmol), the crude product was analyzed by 1H NMR to give cyclohexylbenzene in a yield of 99%. GC analysis gave cyclohexylbenzene in a yield of 99%.
Workup
- filtrationthe reaction mixture was filtered through a pad of Florisil®
- concentrationconcentrated in vacuum
Sources & evidence
- ORD record
- ord-9f8d0e906e434358b2179244f30e36de
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07781599B2
Reaction notes
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