Acetone → Methyl 4-bromo-3-methoxybenzoate

HRID 1244776Notes

Reaction equation

HRID 1244776 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5](C(O)=O)=[CH:4][C:3]=1O.[C:12](=[O:15])([O-])[O-:13].[K+].[K+].COS([O:23][CH3:24])(=O)=O.[CH3:25]C(C)=O>>[CH3:25][O:13][C:12](=[O:15])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[C:3]([O:23][CH3:24])[CH:4]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 14570117Methyl 4-bromo-3-methoxybenzoateYield 47%

Procedure

To a solution of 4-bromo-3-hydroxybenzoic acid (14.480 mmol, 2.600 g) in acetone (180 mL), potassium carbonate (62.988 mmol, 8.710 g) and dimethylsulfate (31.422 mmol, 2.970 mL) were added. The reaction was stirred at RT for 30 minutes and evaporated to dryness. The residue was then diluted with water and extracted with ethyl acetate. The collected organic layer was washed with water and brine, dried (MgSO4), filtered, and concentrated under reduced pressure. 4-Bromo-3-methoxy-benzoic acid methyl ester was isolated by chromatography on silica gel eluting with cyclohexane containing from 0% to 20% ethyl acetate. Yield: 47%.

Workup

  1. customevaporated to dryness
  2. additionThe residue was then diluted with water
  3. extractionextracted with ethyl acetate
  4. washThe collected organic layer was washed with water and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a8ee7393344c49d1af86dea65fab1014
Source dataset
uspto-grants-2006_10
Patent number
US07122565B2

Reaction notes

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