Sulfuric Acid → Methyl 4-Bromo-3-hydroxybenzoate

HRID 639232Notes

Reaction equation

HRID 639232 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 then 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 product as a white solid, m.p. 130-132° C.

Workup

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

Sources & evidence

ORD record
ord-b7746a1a1ab549529cebc0afc0032294
Source dataset
uspto-grants-2010_04
Patent number
US07691848B2

Reaction notes

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