Methanol → methyl 2-bromo-3-methoxybenzoate

HRID 906107Notes

Reaction equation

HRID 906107 reaction equation
[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].S(=O)(=O)(O)O.[CH3:18]O>>[Br:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH3:18])=[O:5]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 1451622-Bromo-3-methoxybenzoic acid

Product 1

HCID 10922803methyl 2-bromo-3-methoxybenzoateYield 80%

Procedure

To a solution of 2-bromo-3-methoxybenzoic acid (718 mg, 3.11 mmol) in methanol (20 mL) was added a catalytic amount of concentrated sulfuric acid and the mixture was brought to reflux for 20 h. On cooling to room temperature, the solution was concentrated and the residue was taken into ethyl acetate and washed with water, saturated aqueous sodium bicarbonate (2×) and brine then dried over sodium sulfate. The solution was then filtered and concentrated to give methyl 2-bromo-3-methoxybenzoate (610 mg, 80%). MS (EI) for C9H9BrO3: 245 (MH+).

Workup

  1. temperatureto reflux for 20 h
  2. concentrationthe solution was concentrated
  3. washwashed with water, saturated aqueous sodium bicarbonate (2×) and brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationThe solution was then filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3e1222baee6d45589bf84b56df0ac187
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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