Methanol → Methyl 3-Bromo-2-methylbenzoate

HRID 1712948Notes

Reaction equation

HRID 1712948 reaction equation
S(=O)(=O)(O)O.[Br:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([OH:12])=[O:11].[CH3:17]O>>[Br:6][C:7]1[C:8]([CH3:16])=[C:9]([CH:13]=[CH:14][CH:15]=1)[C:10]([O:12][CH3:17])=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 27355903-Bromo-2-methylbenzoic Acid

Product 1

HCID 12929135Methyl 3-Bromo-2-methylbenzoateYield 95%

Procedure

Concentrated sulfuric acid (1 mL) was added to a solution of 3-bromo-2-methylbenzoic acid (27.9 mmol) in MeOH (60 mL) at rt. The reaction mixture was allowed to stir at reflux overnight and then concentrated to ˜half volume. The solution was diluted with diethyl ether and washed with saturated NaHCO3 and brine. The organic solution was dried over Na2SO4, filtered and concentrated to give methyl 3-bromo-2-methylbenzoate (27 mmol, 95%) as an oil which was used without further purification.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated to ˜half volume
  3. additionThe solution was diluted with diethyl ether
  4. washwashed with saturated NaHCO3 and brine
  5. dry with materialThe organic solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-30402eac925848d3bf9edc3bfac4f242
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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