m-Chloroperbenzoic acid → HCID 67356126, compound

HRID 1061463Notes

Reaction equation

HRID 1061463 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>[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

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18629366HCID 18629366, compound

Product 1

HCID 67356126HCID 67356126, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

27.26 g of 3-difluoromethyl-2-methylpyridine (XVI) was dissolved in 700 ml of anhydrous dichloromethane, and under cooling with ice, to which 45.19 g of 3-chloro-perbenzoic acid was added, and the resulting mixture was stirred at 5° C. for 12 hours. The resulting organic layer was washed with 5% sodium carbonate solution, and thereafter, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; chloroform:methanol=9:1) to obtain 29.82 g of 3-difluoromethyl-2-methylpyridine N-oxide (XVII).

Workup

  1. additionwas added
  2. washThe resulting organic layer was washed with 5% sodium carbonate solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent; chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-6c283addb8c64065af709e8f1379c14f
Source dataset
uspto-grants-2003_02
Patent number
US06525066B2

Reaction notes

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