Sulfuric Acid → Methyl 4-Bromo-3-hydroxybenzoate

HRID 2244191Notes

Reaction equation

HRID 2244191 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[OH:11].S(=O)(=O)(O)O.[C:17](=O)([O-])[O-].[Na+].[Na+]>CO>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:17])=[O:7])=[CH:4][C:3]=1[OH:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 64209734-Bromo-3-hydroxybenzoic acid

Product 1

HCID 6425184Methyl 4-Bromo-3-hydroxybenzoateYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-bromo-3-hydroxybenzoic acid (30 mmol) in methanol (100 mL) was added concentrated sulfuric acid (2.6 mL). The solution was heated at reflux for 5 hours, cooled to 0° C., and brought to pH 7 by adding saturated. aqueous sodium carbonate. The solution was evaporated to one-third the original volume. Water was added and the product was extracted into ethyl acetate. The organic extracts were washed with water and brine, and dried over anhydrous sodium sulfate. Evaporation gave 6.15 g (89%) of the title compound as a white solid. This was used without further purification.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 5 hours
  3. additionby adding saturated
  4. customThe solution was evaporated to one-third the original volume
  5. additionWater was added
  6. extractionthe product was extracted into ethyl acetate
  7. washThe organic extracts were washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customEvaporation

Sources & evidence

ORD record
ord-f84bc76ef20e4736a89aa8273984b31c
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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