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

HRID 1820829Notes

Reaction equation

HRID 1820829 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].C(=O)([O-])[O-:16].[Cs+].[Cs+].[F:21][C:22]([F:28])([F:27])[CH:23]([CH3:26])[CH2:24]O.C(O)=O>CC(N(C)C)=O>[CH3:14][S:11]([C:8]1[CH:9]=[CH:10][C:2]([O:16][C:23]([CH3:26])([CH3:24])[C:22]([F:28])([F:27])[F:21])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 10796Cesium carbonateHCID 101489933,3,3-Trifluoro-2-methylpropan-1-olHCID 224675662-Fluoro-5-methanesulfonyl-benzoic acid

Product 1

HCID 211003045-Methanesulfonyl-2-(2,2,2-trifluoro-1,1-dimethyl-ethoxy)-benzoic acid

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To 2-Fluoro-5-methanesulfonyl-benzoic acid (247569-56-8) (600 mg) in dimethylacetamide (10 mL) was added cesium carbonate at 170° C. 2-trifluoromethyl-propanol (0.94 mL) was first added to the reaction mixture followed by additionally 0.47 mL every 24 hours. After a total of 72 hours, the reaction mixture was acidified by addition of formic acid, concentrated in vacuo and purified by preparative HPLC to yield the title compound as a light brown solid (897 mg). MS (m/e): 325.3. (M−H, 100%)

Workup

  1. customfollowed by additionally 0.47 mL every 24 hours
  2. concentrationconcentrated in vacuo
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-385f41aa87a744569c80b3804f97d796
Source dataset
uspto-grants-2009_10
Patent number
US07605163B2

Reaction notes

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