Sulfuric Acid → Methyl 5-bromo-2-methylbenzoate

HRID 730169Notes

Reaction equation

HRID 730169 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].S(=O)(=O)(O)O.[CH3:17]OC(=O)C1C=CC=C(Br)C=1C>CO>[CH3:17][O:8][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[CH3:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 3460045-Bromo-2-methylbenzoic acidHCID 12929135Methyl 3-Bromo-2-methylbenzoate

Product 1

HCID 316201Methyl 5-bromo-2-methylbenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude 5-bromo-2-methylbenzoic acid (1) (60.8 g; 283 mmol) was stirred in methanol (400 mL) and concentrated sulfuric acid (6 mL) was added. The mixture was heated at gentle boiling for 20 hours. The solvent was evaporated and the residue was taken up into toluene and water. The solution was shaken and the phases were separated. The organic layer was washed with dilute aqueous NaHCO3, water, and brine. The solution was dried with MgSO4, filtered, and evaporated to get an orange oil. Fractional distillation at reduced pressure yields a mixture of the title compound and 3-bromo-2-methylbenzoic acid methyl ester (47.9 g; 74%).

Workup

  1. temperatureThe mixture was heated at gentle boiling for 20 hours
  2. customThe solvent was evaporated
  3. customthe phases were separated
  4. washThe organic layer was washed with dilute aqueous NaHCO3, water, and brine
  5. dry with materialThe solution was dried with MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto get an orange oil
  9. distillationFractional distillation at reduced pressure
  10. customyields

Sources & evidence

ORD record
ord-317859dbf8934b93a0157aec7bdc02c2
Source dataset
uspto-grants-2009_09
Patent number
US07582667B2

Reaction notes

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