Formic Acid → 5-Methanesulfonyl-2-(2,2,2-trifluoro-1,1-dimethyl-ethoxy)-benzoic acid

HRID 1352255Notes

Reaction equation

F[C:2]1[CH:10]=[CH:9][C:8]([S:11]([CH3:14])(=[O:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:15][C:16]([F:22])([F:21])[C:17]([CH3:20])([OH:19])[CH3:18].C(=O)([O-])[O-].[Cs+].[Cs+].C(O)=O>CN(C)C(=O)C>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([O:19][C:17]([CH3:20])([CH3:18])[C:16]([F:22])([F:21])[F:15])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

Participants

Conditions

Temperature: 170 °C

Procedure

To a solution of 2.75 mmol 2-fluoro-5-methanesulfonyl-benzoic acid in 10 ml N,N-dimethylacetamide were added 14.7 mmol 1,1,1-trifluoro-2-methyl-propan-2-ol and 8.29 mmol cesium carbonate and the mixture was stirred at 170° C. for 72 hours. The reaction mixture was then cooled to room temperature, acidified by addition of formic acid, and then concentrated in vacuo. The residue was purified by preparative HPLC to afford the title compound as a light brown solid (yield 99%). MS (m/e): 325.3. ([M−H]−, 100%)

Workup

temperatureThe reaction mixture was then cooled to room temperature
concentrationconcentrated in vacuo
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-fd6b08ad145e439faaa7ac162740fc89
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220744B2

Reaction notes

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