Hydrochloric Acid → 2,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamide

HRID 508427Notes

Reaction equation

HRID 508427 reaction equation
C([O:5][C:6]1[C:18]([F:19])=[CH:17][C:9]([C:10]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[O:11])=[C:8]([F:20])[CH:7]=1)(C)(C)C.Cl>O1CCOCC1>[F:20][C:8]1[CH:7]=[C:6]([OH:5])[C:18]([F:19])=[CH:17][C:9]=1[C:10]([NH:12][S:13]([CH3:16])(=[O:14])=[O:15])=[O:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 580423914-tert-butoxy-2,5-difluoro-N-(methylsulfonyl)benzamide

Product 1

HCID 580424162,5-difluoro-4-hydroxy-N-(methylsulfonyl)benzamideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-tert-Butoxy-2,5-difluoro-N-(methylsulfonyl)benzamide (Preparation 17, 1.76 g, 5.73 mmol) was added to hydrochloric acid solution in dioxane (4 M, 30 mL) at room temperature and stirred for 3 hours. The solvent was then evaporated and the resulting residue dissolved in DCM. The solvent was evaporated again to yield the title compound as a white solid (1.4 g, 100%), which was used in the next stage without further purification.

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe resulting residue dissolved in DCM
  3. customThe solvent was evaporated again

Sources & evidence

ORD record
ord-860ead2e9f174413a7bec1b7c55d3df6
Source dataset
uspto-grants-2015_08
Patent number
US09096500B2

Reaction notes

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