Methanol → HCID 66959475, compound

HRID 215715Notes

Reaction equation

HRID 215715 reaction equation
S(=O)(=O)(O)O.[F:6][C:7]1[C:15]([S:16][CH3:17])=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[CH3:22]O>>[F:6][C:7]1[C:15]([S:16][CH3:17])=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=[CH:12][C:8]=1[C:9]([O:11][CH3:22])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 669577352-Fluoro-3-(methylthio)-4-(trifluoromethyl)benzoic acid

Product 1

HCID 66959475HCID 66959475, compound

Procedure

5 ml of concentrated sulfuric acid were added to 20.0 g (78.7 mmol) of 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoic acid in 200 ml of methanol, and the mixture was heated under reflux until HPLC analysis showed complete conversion. The mixture was cooled and the solvent was removed. The residue was taken up in water, and the mixture was extracted twice with ethyl acetate. The combined organic phases were washed once with saturated aqueous NaHCO3 solution. Finally, the organic phase was dried and the filtrate was concentrated. This gave 20.5 g of methyl 2-fluoro-3-methylthio-4-(trifluoromethyl)benzoate.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux until HPLC analysis
  3. temperatureThe mixture was cooled
  4. customthe solvent was removed
  5. extractionthe mixture was extracted twice with ethyl acetate
  6. washThe combined organic phases were washed once with saturated aqueous NaHCO3 solution
  7. customFinally, the organic phase was dried
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-441fd5a40e5a491e9591a4fa948bd5ae
Source dataset
uspto-grants-2012_06
Patent number
US08193121B2

Reaction notes

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