Dimethyl Sulfate → Methyl 5-bromo-2-methoxybenzoate

HRID 646274Notes

Reaction equation

HRID 646274 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](O)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O>CC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:12])=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 69725-Bromosalicylic acidHCID 11430Potassium Carbonate

Product 1

HCID 13297188Methyl 5-bromo-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5-Bromo-2-hydroxybenzoic acid (25 g) and 40 g of potassium carbonate were suspended in 300 mL of acetone. Dimethyl sulfate (28 mL) was added to the suspension, and the mixture was stirred for 19 hours under reflux with heating. The reaction mixture was cooled to room temperature, whereafter the insolubles were separated by filtration, and washed with ethyl acetate. The filtrate and the washings were combined, and acetone and ethyl acetate were distilled off under reduced pressure. The resulting residue was dissolved in 300 mL of ethyl acetate. Water (300 mL) was added to the solution, and the organic layer was separated; followed by extracting the aqueous layer with 200 mL of ethyl acetate. After the respective organic layers were combined, the combined organic layer was washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was separated by filtration, and then washed with ethyl acetate. The filtrate and the washings were combined, and ethyl acetate was distilled off under reduced pressure to obtain 30 g of methyl 5-bromo-2-methoxybenzoate.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating
  3. customwere separated by filtration
  4. washwashed with ethyl acetate
  5. distillationacetone and ethyl acetate were distilled off under reduced pressure
  6. dissolutionThe resulting residue was dissolved in 300 mL of ethyl acetate
  7. additionWater (300 mL) was added to the solution
  8. customthe organic layer was separated
  9. extractionby extracting the aqueous layer with 200 mL of ethyl acetate
  10. washthe combined organic layer was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over anhydrous sodium sulfate
  12. customThe anhydrous sodium sulfate was separated by filtration
  13. washwashed with ethyl acetate
  14. distillationethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d6d1a8834a9345d3a04b8c171dab07e1
Source dataset
uspto-grants-2010_04
Patent number
US07705053B2

Reaction notes

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