Hydrogen Peroxide → HCID 19066096, compound

HRID 1467404Notes

Reaction equation

HRID 1467404 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 water, neutralized with solid Na2CO3 with stirring, and extracted with ethyl acetate three times. The combined organic layer was dried over anhydrous Na2SO4, filtered, concentrated, and dried to give 1.67 g of analytically pure 2-chloro-4-trifluoromethylpyridine N-oxide 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: 197 [M]+.

Workup

  1. additionThe reaction mixture was poured into ice-cold water
  2. stirringwith stirring
  3. extractionextracted with ethyl acetate 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-86bc01a6775146f98633efa55c1a5562
Source dataset
uspto-grants-2015_04
Patent number
US09000162B2

Reaction notes

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