Sulfuric Acid → Methyl 2,5-dibromo-4-methylbenzoate

HRID 1667328Notes

Reaction equation

HRID 1667328 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[C:18](OCC)(=O)C>CO>[Br:1][C:2]1[CH:10]=[C:9]([CH3:11])[C:8]([Br:12])=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 232948852,5-Dibromo-4-methylbenzoic acid

Product 1

HCID 26338328Methyl 2,5-dibromo-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,5-dibromo-4-methylbenzoic acid 5.88 g, 20 mmol) in 50 mL of methanol was added 0.2 mL of concentrated sulfuric acid. The resulting solution was refluxed for 24 hours. Evaporation of the solvent gave a residue, which was redissolved into 100 mL of ethyl acetate. The organic layer was washed with saturated sodium biocarbonate solution, water and brine. The resulting organic layer was dried over sodium sulfate. Filtration off sodium sulfate and evaporation of the solvent gave methyl 2,5-dibromo-4-methylbenzoate as a white solid: 6.20 g (100%).

Workup

  1. temperatureThe resulting solution was refluxed for 24 hours
  2. customEvaporation of the solvent
  3. customgave a residue, which
  4. washThe organic layer was washed with saturated sodium biocarbonate solution, water and brine
  5. dry with materialThe resulting organic layer was dried over sodium sulfate
  6. filtrationFiltration
  7. customoff sodium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-83edb0e976ef4969932a94916f9cc6dc
Source dataset
uspto-grants-2011_10
Patent number
US08044212B2

Reaction notes

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