Hydrogen Peroxide → HCID 19066096, compound

HRID 1409297Notes

Reaction equation

HRID 1409297 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][N:3]=1.OO.C([O-])([O-])=[O:15].[Na+].[Na+]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:5]=[CH:4][N+:3]=1[O-:15]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 1449582-Chloro-4-(trifluoromethyl)pyridine

Product 1

HCID 19066096HCID 19066096, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-chloro-4-trifluoromethylpyridine (1.81 g, 10 mmol) in trifluoroacetic acid (12 mL) was added 30% hydrogen peroxide (8 mL), and the mixture was stirred at 50° C. over a weekend. The reaction mixture was poured into ice-cold H2O, neutralized with solid Na2CO3 with stirring, and extracted with EtOAc three times. The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated, and dried to give analytically pure 2-chloro-4-trifluoromethylpyridine N-oxide (1.67 g) as a brown oil: 1H NMR (CDCl3) δ 8.45 (d, J=6.9 Hz, 1H), 7.77 (d, J=2.4 Hz, 1H), 7.47 (dd, J=6.9, 2.4 Hz, 1H); GC-MS m/z 197 ([M]+).

Workup

  1. additionThe reaction mixture was poured into ice-cold H2O
  2. stirringwith stirring
  3. extractionextracted with EtOAc three times
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried

Sources & evidence

ORD record
ord-52dff169762c4eedbefe01853d0935c1
Source dataset
uspto-grants-2014_12
Patent number
US08921382B2

Reaction notes

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