Water → 4-tert-butoxy-2,5-difluoro-N-(methylsulfonyl)benzamide

HRID 2048060Notes

Reaction equation

HRID 2048060 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[F:7][C:8]1[CH:20]=[C:19](F)[C:18]([F:22])=[CH:17][C:9]=1[C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:11].O>CS(C)=O.CCOC(C)=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[C:2]([O:4][C:19]1[C:18]([F:22])=[CH:17][C:9]([C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:11])=[C:8]([F:7])[CH:20]=1)([CH3:5])([CH3:3])[CH3:1]

Participants

7

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxide2×HCID 580424352,4,5-trifluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 580423914-tert-butoxy-2,5-difluoro-N-(methylsulfonyl)benzamideYield 100%

Reagents, catalysts & solvents 3

HCID 311Citric AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-butoxide (1.46 g, 13.0 mmol) was added to a solution of 2,4,5-trifluoro-N-(methylsulfonyl)benzamide (Preparation 27, 1.5 g, 5.924 mmol) in DMSO (10 mL) and stirred at room temperature. After 3 hours, potassium tert-butoxide (140 mg, 1.3 mmol) was further added and stirred for 18 hours more. The reaction mixture was diluted with EtOAc and 10% aqueous citric acid solution. The pH of the water layer was acidic. The organic layer was washed with more 10% aqueous citric acid and brine, then dried over magnesium sulfate, filtered and concentrated in vacuo to yield the title compound as a cream solid (1.76 g, 100%):

Workup

  1. stirringstirred for 18 hours more
  2. washThe organic layer was washed with more 10% aqueous citric acid and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdf211b9727144abae5c27e6e0d3cd30
Source dataset
uspto-grants-2013_11
Patent number
US08592629B2

Reaction notes

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