1-Bromo-4-methoxy-2-methylbenzene → 1-Cyclohexyl-4-methoxy-2-methylbenzene
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10]>CC(P(C(C)(C)C)C(C)(C)C)(C)C.CC(P(C(C)(C)C)C(C)(C)C)(C)C.[Pd]>[CH:2]1([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=2[CH3:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
1-Bromo-4-methoxy-2-methyl-benzene (520 mg, 2.6 mmol) is dissolved in cyclohexylzinc bromide THF solution (0.5 M, 15 mL) in a microwave tube. Pd(t-Bu3P)2 (66 mg, 0.13 mmol, 0.05 eq.) is added to this solution. The mixture is purged with N2 (g) for 5 minutes and heated at 100° C. for 30 minutes using microwave irradiation. Upon completion, the reaction mixture is diluted with EtOAc, washed with 1 N HCl (aq), brine, filtered through celite, and dried over Na2SO4. After concentration, the residue is partially purified by silica gel chromatography (5% EtOAc in hexanes) to give crude 1-cyclohexyl-4-methoxy-2-methyl-benzene.
Workup
- customThe mixture is purged with N2 (g) for 5 minutes
- custommicrowave irradiation
- additionUpon completion, the reaction mixture is diluted with EtOAc
- washwashed with 1 N HCl (aq), brine
- filtrationfiltered through celite
- dry with materialdried over Na2SO4
- concentrationAfter concentration
- customthe residue is partially purified by silica gel chromatography (5% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-eb65aeab8c5c4025ab1bdf22942ff68d
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572811B2
Reaction notes
Loading…