Ethyl Acetate → Methyl 4-bromo-3-methoxybenzoate

HRID 1051847Notes

Reaction equation

HRID 1051847 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[OH:12].[C:13](=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C.IC>[Br:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6425184Methyl 4-Bromo-3-hydroxybenzoate

Product 1

HCID 14570117Methyl 4-bromo-3-methoxybenzoateYield 94.3%

Reagents, catalysts & solvents 2

HCID 6328Methyl iodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 4-bromo-3-hydroxybenzoate (10.0 g) in DMF (50 mL) was added potassium carbonate (17.9 g) and iodomethane (9.2 mg). The mixture was stirred at room temperature for 2 h. Ethyl acetate was added and the mixture was washed with water. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum to give 10 g of the title compound, that was used without further purification.

Workup

  1. washthe mixture was washed with water
  2. washThe organic phase was washed with saturated sodium chloride solution
  3. dry with materialdried (sodium sulfate)
  4. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-4bb7014a76804ee0b1e82b7ee48d91b7
Source dataset
uspto-grants-2016_07
Patent number
US09388177B2

Reaction notes

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