Methanol → Methyl 2-bromo-5-methoxybenzoate

HRID 1057469Notes

Reaction equation

HRID 1057469 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:18]O>>[Br:6][C:7]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:8]=1[C:9]([O:11][CH3:18])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 899062-Bromo-5-methoxybenzoic acid

Product 1

HCID 2776849Methyl 2-bromo-5-methoxybenzoate

Procedure

Sulfuric acid (2 eq) was added to a solution of 2-bromo-5-methoxybenzoic acid (1 eq) in methanol (0.30 M) at 0° C. under N2. The solution was allowed to warm to RT and then refluxed for 5 h. After cooling to RT, the solution was concentrated in vacuo, the residue dissolved in ethyl acetate and washed with 1N NaOH solution (2×). The combined aqueous layers were extracted with ethyl acetate and the combined organics dried over MgSO4. Concentration in vacuo gave methyl 2-bromo-5-methoxybenzoate as a clear oil. EI-MS m/z 245, 247 (M+H)+

Workup

  1. temperaturerefluxed for 5 h
  2. temperatureAfter cooling to RT
  3. concentrationthe solution was concentrated in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washwashed with 1N NaOH solution (2×)
  6. extractionThe combined aqueous layers were extracted with ethyl acetate
  7. dry with materialthe combined organics dried over MgSO4
  8. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-c46c081e94f4456e8c0dd4d2088cce0d
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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