2-Bromopropane → Methyl 2-(4-bromophenyl)-3-methylbutanoate

HRID 547981Notes

Reaction equation

HRID 547981 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1.[CH3:13][C:14](C)([O-])[CH3:15].[K+].C(Br)(C)C>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[CH:4]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)[CH:14]([CH3:15])[CH3:13]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 316783Methyl 2-(4-bromophenyl)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 46855859Methyl 2-(4-bromophenyl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The (4-bromophenyl)acetic acid methyl ester in the Step 1 and potassium t-butoxide (4.8 g, 1 eq) were dissolved in 200 ml DMF at 0° C. Isopropyl bromide (4 ml. 1 eq) was added into the mixture and stirred at room temperature for 3 hours. When the reaction was completed, the mixture was extracted 3 times with ethyl acetate and water, and washed with saline solution. After the organic layer was dried with anhydrous and the solvent was removed at low pressures, the target compound 2-(4-bromophenyl)3-methylbutyric acid methyl ester was obtained by separation and purification of the mixture using a column chromatography (ethyl acetate:n-hexane=1:10) (6.60 g, 57%).

Workup

  1. extractionthe mixture was extracted 3 times with ethyl acetate and water
  2. washwashed with saline solution
  3. customAfter the organic layer was dried with anhydrous and the solvent
  4. customwas removed at low pressures

Sources & evidence

ORD record
ord-d6dda329598045ae8ef0c73881bba2ed
Source dataset
uspto-grants-2011_05
Patent number
US07939672B2

Reaction notes

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