4-(4-Bromo-3,5-dimethylphenyl)butan-2-one → 4-(4-Bromo-3,5-dimethylphenyl)-2-methylbutan-2-ol

HRID 237537Notes

Reaction equation

HRID 237537 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11](=[O:13])[CH3:12])=[CH:4][C:3]=1[CH3:14].[CH3:15][Mg]Br>O1CCCC1.O1CCCC1.C1(C)C=CC=CC=1>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][C:11]([CH3:15])([OH:13])[CH3:12])=[CH:4][C:3]=1[CH3:14]

Participants

5

Reactant 2

HCID 866971994-(4-Bromo-3,5-dimethylphenyl)butan-2-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 866972004-(4-Bromo-3,5-dimethylphenyl)-2-methylbutan-2-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

To a solution of 4-(4-bromo-3,5-dimethylphenyl)butan-2-one (100 mg) in tetrahydrofurane (2 mL) is added at 0° C. methylmagnesium bromide (840 μL of a 1.4 M solution in tetrahydrofurane/toluene 1:3). The mixture is stirred for 2 hours while warming to room temperature and then partitioned between saturated aqueous NH4Cl solution and diethylether. The organic phase is dried (MgSO4) and concentrated to give the title compound. Yield: 105 mg; LC (method 8): tR=0.47 min; Mass spectrum (ESI+): m/z=271 [M+H]+.

Workup

  1. custompartitioned between saturated aqueous NH4Cl solution and diethylether
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a0564b10aa0c429bbf5205f2791e2313
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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