m-Chloroperbenzoic acid → HCID 67356126, compound

HRID 2385132Notes

Reaction equation

HRID 2385132 reaction equation
[F:1][CH:2]([F:10])[C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[CH:7][CH:8]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>ClCCl.[OH-].[Na+]>[F:1][CH:2]([F:10])[C:3]1[C:4]([CH3:9])=[N+:5]([O-:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18629366HCID 18629366, compound

Product 1

HCID 67356126HCID 67356126, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-(difluoromethyl)-2-methylpyridine (2.56 g, 17.9 mmol) in dichloromethane was added 3-chloroperbenzoic acid (6.01 g, 26.8 mmol) at ambient temperature. After stirring for 2 h, the mixture was diluted with a 1 M aqueous sodium hydroxide (50 mL) and extracted with dichloromethane (4×50 mL). The organic phase was washed with brine (150 mL), dried over sodium sulfate, filtered and concentrated in vacuo to afford 3-(difluoromethyl)-2-methylpyridine-1-oxide as a yellow oil (2.22 g, 78%): 1H NMR (300 MHz, CDCl3) δ8.36 (d, J=6.5 Hz, 1H), 7.40 (d, J=7.9 Hz, 1H), 7.23 (m, 1H), 6.80-6.70 (m, 1H), 2.57 (s, 3H).

Workup

  1. extractionextracted with dichloromethane (4×50 mL)
  2. washThe organic phase was washed with brine (150 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f236f01f6f314f1cbeea9af3b8052c13
Source dataset
uspto-grants-2012_09
Patent number
US08263606B2

Reaction notes

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