m-Chloroperbenzoic acid → Pyridine, 4-(difluoromethyl)-, 1-oxide

HRID 1057034Notes

Reaction equation

HRID 1057034 reaction equation
[F:1][CH:2]([F:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=[O:18])C=1>C(Cl)Cl>[F:1][CH:2]([F:9])[C:3]1[CH:8]=[CH:7][N+:6]([O-:18])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 6404764-(Difluoromethyl)pyridine

Product 1

HCID 90015270Pyridine, 4-(difluoromethyl)-, 1-oxideYield 100.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-difluoromethylpyridine (5.00 g, 38.7 mmol) in CH2Cl2 (77 mL, 0.5 M) at 0° C. was added 77% meta-chloroperbenzoic acid (10.7 g, 46.5 mmol) and the ice bath was removed and stirring continued for 20.5 hr. The reaction mixture was concentrated to dryness and reaction residue purified by flash column chromatography (100:0-95:5 CH2Cl2/MeOH) to afford 4-difluoromethyl-pyridine-N-oxide as a colorless solid (5.62 g, >99%); 1H NMR (400 MHz, CDCl3) δ 8.26 (d, J=6.4 Hz, 2H), 7.40 (d, J=6.4 Hz, 2H), 6.63 (t, J=55.7 Hz, 1H).

Workup

  1. customthe ice bath was removed
  2. concentrationThe reaction mixture was concentrated to dryness and reaction residue
  3. custompurified by flash column chromatography (100:0-95:5 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-665fb505acf94b37b12d15377c12f219
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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