Sulfuric Acid → Methyl 4-bromo-2-methylbenzoate

HRID 1041920Notes

Reaction equation

HRID 1041920 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([CH3:16])[CH:8]=1.[C:17](=O)([O-])O.[Na+]>CO>[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([O:13][CH3:17])=[O:12])=[C:9]([CH3:16])[CH:8]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 995704-Bromo-2-methylbenzoic acidHCID 516892Sodium Bicarbonate

Product 1

HCID 22031226Methyl 4-bromo-2-methylbenzoateYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

Concentrated sulfuric acid (500 μL) was added to a methanol (20.0 mL) solution of 4-bromo-2-methylbenzoic acid (2.00 g, 9.30 mmol), and the mixture was stirred for 5 hours at 80° C. The reaction mixture was cooled to room temperature, subsequently a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, and the mixture was subjected to extraction two times with ethyl acetate. The organic layer thus obtained was washed once with saturated brine, and was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and thus, the title compound (2.02 g, yield: 95%) was obtained.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe mixture was subjected to extraction two times with ethyl acetate
  3. customThe organic layer thus obtained
  4. washwas washed once with saturated brine
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9fe9ed4b88fa4ca99c36e4da968f56f9
Source dataset
uspto-grants-2013_10
Patent number
US08557802B2

Reaction notes

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