Methanol → Methyl 3-bromo-2-methoxybenzoate

HRID 655996Notes

Reaction equation

HRID 655996 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:8]([O:16][CH3:17])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].[CH3:18]O>>[CH3:18][O:11][C:10](=[O:12])[C:9]1[CH:13]=[CH:14][CH:15]=[C:7]([Br:6])[C:8]=1[O:16][CH3:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 2535983-Bromo-2-methoxybenzoic acid

Product 1

HCID 46311082Methyl 3-bromo-2-methoxybenzoate

Procedure

5.0 mL of sulfuric acid (H2SO4) was slowly added to a solution of 5.0 g of 3-bromo-2-methoxy-benzoic acid 4 in 100 mL of methanol (MeOH). The resulting solution was heated to reflux overnight. The solution was cooled to room temperature and quenched with sodium bicarbonate to pH 7. The aqueous layer was extracted several times with ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulphate. The resulting mixture was filtered. The solvents were evaporated under reduced pressure to afford 5.3 g of 3-bromo-2-methoxy-benzoic acid methyl ester 5.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux overnight
  3. customquenched with sodium bicarbonate to pH 7
  4. extractionThe aqueous layer was extracted several times with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationThe resulting mixture was filtered
  8. customThe solvents were evaporated under reduced pressure

Sources & evidence

ORD record
ord-9241bc404e4f49a2bc303f319c431a23
Source dataset
uspto-grants-2011_12
Patent number
US08071636B2

Reaction notes

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