Water → Methyl 4-bromo-3-methoxybenzoate

HRID 2244192Notes

Reaction equation

HRID 2244192 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1O.[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O.O>CC(C)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:12])=[O:7])=[CH:4][C:3]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 14570117Methyl 4-bromo-3-methoxybenzoateYield 99%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-bromo-3-hydroxybenzoic acid of Step A (27 mmol), potassium carbonate (33 mmol) and dimethyl sulfate (32 mmol), in acetone (40 mL) was stirred at reflux temperature under nitrogen atmosphere for three hours. The mixture was cooled and 5 mL of water was added. The acetone was evaporated and 30 mL of water was added. The product was extracted into dichloromethane. The organic solution was dried over anhydrous magnesium sulfate, and evaporated to provide the title compound (6.5 g; 99%) as a hard, white, crystalline solid.

Workup

  1. temperatureat reflux temperature under nitrogen atmosphere for three hours
  2. temperatureThe mixture was cooled
  3. customThe acetone was evaporated
  4. addition30 mL of water was added
  5. extractionThe product was extracted into dichloromethane
  6. dry with materialThe organic solution was dried over anhydrous magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-8af6349f01aa42ef888446141aaa455e
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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