m-Chloroperbenzoic acid → HCID 67272534, compound

HRID 250946Notes

Reaction equation

HRID 250946 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:18].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]([F:11])([F:12])[F:10])=[CH:4][N+:3]=1[O-:18]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 57675244HCID 57675244, compound

Product 1

HCID 67272534HCID 67272534, compoundYield 81.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,3-dimethyl-5-trifluoromethyl-pyridine (0.700 g, 4.00 mmol), 3-chloroperoxybenzoic acid (77%, 2.8 g, 12 mmol) in CH2Cl2 (20 mL) was stirred at room temperature for 20 h. After that period of time saturated aqueous NaHCO3 (5 mL), and the mixture was extracted with CH2Cl2 (5×20 mL). The extracts were combined and dried over Na2SO4. After filtration the solvent was removed, and the residue was purified on silica gel column (EtOAc), affording 2,3-dimethyl-5-trifluoromethyl-pyridine 1-oxide as a pale yellow solid (0.620 g, 81%).

Workup

  1. extractionthe mixture was extracted with CH2Cl2 (5×20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationAfter filtration the solvent
  4. customwas removed
  5. customthe residue was purified on silica gel column (EtOAc)

Sources & evidence

ORD record
ord-ae4967842d1a46559e57847df3e7d549
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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