Sulfuric Acid → Methyl 2-bromo-5-methylbenzoate

HRID 493100Notes

Reaction equation

HRID 493100 reaction equation
OS(O)(=O)=O.[Br:6][C:7]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[C:17]([O-])(O)=O.[Na+]>CO>[CH3:17][O:10][C:9](=[O:11])[C:8]1[CH:12]=[C:13]([CH3:16])[CH:14]=[CH:15][C:7]=1[Br:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 2280802-Bromo-5-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 15110996Methyl 2-bromo-5-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1 mL H2SO4 is added to 2-bromo-5-methyl-benzoic acid (7.5 g, 70 mmol) in 75 mL methanol. The reaction mixture is refluxed 16 hours and cooled to room temperature. 100 mL saturated NaHCO3 (aq) is added. Methanol is removed in vacuo. The resulting mixture is extracted with ethyl acetate. The organic phase is washed with brine, dried with MgSO4 and concentrated in vacuo to give the title compound.

Workup

  1. temperatureThe reaction mixture is refluxed 16 hours
  2. customMethanol is removed in vacuo
  3. extractionThe resulting mixture is extracted with ethyl acetate
  4. washThe organic phase is washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bfcd936e4a23462d97e62df7c994efd1
Source dataset
uspto-grants-2009_05
Patent number
US07534791B2

Reaction notes

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