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

HRID 237535Notes

Reaction equation

HRID 237535 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:4][C:3]=1[CH3:13].[CH3:14][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][CH:11]([OH:12])[CH3:14])=[CH:4][C:3]=1[CH3:13]

Participants

5

Reactant 2

HCID 866971973-(4-Bromo-3,5-dimethylphenyl)propanalHCID 178418573HCID 178418573, compound

Product 1

HCID 866971984-(4-Bromo-3,5-dimethylphenyl)butan-2-ol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22635083Tetrahydrofuran tolueneSolvent

Procedure

To a solution of 3-(4-bromo-3,5-dimethylphenyl)propanal (120 mg) in tetrahydrofurane (2 mL) is added at 0° C. methylmagnesium bromide (800 μL of a 1.4 M solution in tetrahydrofurane/toluene 1:3). After stirring for 30 minutes the mixture is partitioned between saturated aqueous NH4Cl solution and diethylether. The organic phase is dried (MgSO4) and concentrated. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30) to give the title compound. Yield: 130 mg; LC (method 8): tR=0.37 min; Mass spectrum (ESI+): m/z=274 [M+NH4]+.

Workup

  1. customis partitioned between saturated aqueous NH4Cl solution and diethylether
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 99:1→70:30)

Sources & evidence

ORD record
ord-2fb53238ba8341e48202e44c417eaf41
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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