m-Chloroperbenzoic acid → Pyridine, 2-methyl-5-(trifluoromethyl)-, 1-oxide

HRID 1720364Notes

Reaction equation

HRID 1720364 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:20])C=1.[OH-].[Ca+2].[OH-]>C(Cl)(Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:9])([F:11])[F:10])=[CH:4][N+:3]=1[O-:20]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 6093208Calcium HydroxideHCID 183618732-Methyl-5-(trifluoromethyl)pyridine

Product 1

HCID 54092362Pyridine, 2-methyl-5-(trifluoromethyl)-, 1-oxideYield 146%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of crude 2-methyl-5-trifluoromethylpyridine from Step 1 (3.8 g) in CHCl3 (40 mL) was added m-chloroperbenzoic acid (3.0 g, 17.4 mmol) and the resulting mixture was stirred 5 hours at r.t. More peracid (1.5 g, 8.7 mmol) was added and the reaction stirred another 2 hours. Calcium hydroxide (3.0 g, 40.5 mmol) was added and the slurry was vigorously stirred 20 minutes before filtering through celite. Evaporation of the solvents gave 4.5 g of the title compound containing a little dioxane and CHCl3. This material was used without further purification.

Workup

  1. stirringthe reaction stirred another 2 hours
  2. waitthe slurry was vigorously stirred 20 minutes
  3. filtrationbefore filtering through celite
  4. customEvaporation of the solvents

Sources & evidence

ORD record
ord-9ae6b9509da8490f8ad07dfeccd626eb
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

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