Hydrogen Peroxide → HCID 58174119, compound

HRID 339811Notes

Reaction equation

HRID 339811 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[CH3:9])[CH:5]=[CH:4][N:3]=1.[OH:12]O>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:10])([F:11])[CH3:9])[CH:5]=[CH:4][N+:3]=1[O-:12]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 457909512-Chloro-4-(1,1-difluoroethyl)pyridine

Product 1

HCID 58174119HCID 58174119, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 1.27 g (7 mmol) 2-chloro-4-(1,1-difluoro)ethylpyridine (Preparation 4) in TFA was added 30% hydrogen peroxide (6 mL) and the solution was heated at reflux for 2.5 h. The TFA was removed in vacuo and the residue poured into ice-cold H2O. The mixture was neutralized with Na2CO3 and extracted with EtOAc and CH2Cl2. The pooled organic layers were dried (Na2SO4), filtered and concentrated in vacuo to give 2-chloro-4-(1,1-difluoroethyl)-pyridine 1-oxide (1.00 g) as a brown oil: 1H NMR (CDCl3): δ 8.39 (d, J=6.6 Hz, 1H), 7.63 (d, J=2.4 Hz, 1H), 7.33 (dd, J=6.6, 2.4 Hz, 1H), 1.94 (t, J=18 Hz, 3H); EIMS m/z 193 ([M]+).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 2.5 h
  3. customThe TFA was removed in vacuo
  4. additionthe residue poured into ice-cold H2O
  5. extractionextracted with EtOAc and CH2Cl2
  6. dry with materialThe pooled organic layers were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e58df3aeb5ac4678b9668898b0eb32ef
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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