Hydrogen Peroxide → HCID 58174119, compound

HRID 2386913Notes

Reaction equation

HRID 2386913 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>FC(F)(F)C(O)=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 2-chloro-4-(1,1-difluoro)ethylpyridine (1.27 g, 7 mmol) in trifluoroacetic acid was added 30% hydrogen peroxide (6 mL) and the solution was heated at reflux 2.5 h. The reaction was concentrated in vacuo and the residue poured into ice-cold water. The mixture was neutralized with Na2CO3 and then extracted with EtOAc and CH2Cl2. The pooled organic layers were 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). GC/MS: m/z 193 [M+].

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux 2.5 h
  3. concentrationThe reaction was concentrated in vacuo
  4. additionthe residue poured into ice-cold water
  5. extractionextracted with EtOAc and CH2Cl2
  6. filtrationThe pooled organic layers were filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afe3f3f39d7e4bd0a6d389a88b8dc0ab
Source dataset
uspto-grants-2012_09
Patent number
US08268843B2

Reaction notes

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