Water → Methyl 4-bromo-3-methoxybenzoate

HRID 639233Notes

Reaction equation

HRID 639233 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[C:13](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O.O>CC(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methyl 4-bromo-3-hydroxybenzoate 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, filtered and evaporated to give 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. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-2593850dd9674d17bf5ed3aa83690596
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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