Potassium bisulfate → 5-Bromo-1-(difluoromethyl)-1,2-dihydropyridin-2-one

HRID 2069843Notes

Reaction equation

HRID 2069843 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4]/[C:5](=N\C(=O)C)/[N:6]([CH:8]([F:10])[F:9])[CH:7]=1.[OH:15]S([O-])(=O)=O.[K+]>CC#N.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5](=[O:15])[N:6]([CH:8]([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 516920Potassium bisulfateHCID 178474078HCID 178474078, compound

Product 1

HCID 231159945-Bromo-1-(difluoromethyl)-1,2-dihydropyridin-2-oneYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of the crude N-[5-Bromo-1-difluoromethyl-1H-pyridin-(2E)-ylidene]-acetamide (1 g) in 10 ml CH3CN was added 1% KHSO4 in water (10 ml). The reaction mixture was heated at reflux for 3 hrs. The reaction mixture was cooled down and the solvent was removed under reduced pressure. Without any workup this crude was purified by column chromatography using 10% ethyl acetate in hexane to get 5-Bromo-1-difluoromethyl-1H-pyridin-2-one (550 mg, 52%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 hrs
  3. temperatureThe reaction mixture was cooled down
  4. customthe solvent was removed under reduced pressure
  5. customWithout any workup this crude was purified by column chromatography

Sources & evidence

ORD record
ord-e8a9e79139db415489562e427fff2311
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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