Potassium Carbonate → 5-Methylsulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid methyl ester

HRID 2251233Notes

Reaction equation

HRID 2251233 reaction equation
[CH3:1][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>[CH3:1][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[O:14][CH:18]([CH3:19])[C:17]([F:29])([F:28])[F:16]

Participants

5

Reactant 3

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

Product 1

HCID 588633505-Methylsulfonyl-2-(2,2,2-trifluoro-1-methylethoxy)benzoic acid methyl ester

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 hours. 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-1311ebb01e614676a8f65c20dec5d26b
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

Loading…