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

HRID 512080Notes

Reaction equation

HRID 512080 reaction equation
Cl.C([O:6][C:7]1[C:19]([F:20])=[CH:18][C:10]([C:11]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[O:12])=[C:9]([F:21])[CH:8]=1)(C)(C)C>O1CCOCC1>[F:21][C:9]1[CH:8]=[C:7]([OH:6])[C:19]([F:20])=[CH:18][C:10]=1[C:11]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[O:12]

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 103.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydrochloric acid solution in dioxane (4 M, 30 mL) was added to the 4-tert-butoxy-2,5-difluoro-N-(methylsulfonyl)benzamide (Preparation 109, 1.76 g, 5.73 mmol) and the resulting solution stirred at room temperature. After 3 hours the reaction mixture was concentrated in vacuo and the residue azeotroped repeatedly with DCM to yield the title compound as a white solid (1.49 g, 100%).

Workup

  1. concentrationAfter 3 hours the reaction mixture was concentrated in vacuo
  2. customthe residue azeotroped repeatedly with DCM

Sources & evidence

ORD record
ord-d964ac9ce6614598bd640008a2be1ee3
Source dataset
uspto-grants-2015_08
Patent number
US09102621B2

Reaction notes

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