Potassium Carbonate → (S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acid

HRID 2117455Notes

Reaction equation

HRID 2117455 reaction equation
C[O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10]([CH3:13])(=[O:12])=[O:11])[CH:7]=[CH:6][C:5]=1[OH:14].[F:16][C:17]([F:29])([F:28])[CH:18](OS(C(F)(F)F)(=O)=O)[CH3:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][S:10]([C:8]1[CH:7]=[CH:6][C:5]([O:14][C@@H:18]([CH3:19])[C:17]([F:29])([F:28])[F:16])=[C:4]([CH:9]=1)[C:3]([OH:2])=[O:15])(=[O:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 235031632-Hydroxy-5-methylsulfonylbenzoic acid methyl esterHCID 574452801, 1, 1-Trifluoropropan-2-yl trifluoromethanesulfonatc

Product 1

HCID 58863351(S)-2-(1-Methyl-2,2,2-trifluoroethoxy)-5-methylsulfonylbenzoic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 21.7 mmol 2-hydroxy-5-methanesulfonyl-benzoic acid methyl ester [68029-77-6], 32.5 mmol trifluoro-methanesulfonic acid 2,2,2-trifluoro-1-methyl-ethyl ester [212556-43-9], 43.4 mmol potassium carbonate in 87 ml DMF was stirred at 80° C. for 48 hour After cooling to RT, the mixture was concentrated in vacuo, taken in water and stirred for 1 hour. Filtration yielded the title compound.

Workup

  1. temperatureAfter cooling to RT
  2. concentrationthe mixture was concentrated in vacuo
  3. stirringstirred for 1 hour
  4. filtrationFiltration

Sources & evidence

ORD record
ord-3dfe9e21677d4160a6b1c2c188276a4a
Source dataset
uspto-grants-2008_10
Patent number
US07442710B2

Reaction notes

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