m-Chloroperbenzoic acid → Pyridine, 2-(4-fluorophenyl)-3-methyl-, 1-oxide

HRID 2095786Notes

Reaction equation

HRID 2095786 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:23])C=1>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N+:9]=2[O-:23])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 136013722-(4-Fluorophenyl)-3-methylpyridine

Product 1

HCID 58158491Pyridine, 2-(4-fluorophenyl)-3-methyl-, 1-oxideYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(4-fluorophenyl)-3-methylpyridine (26.8 g, 0.143 mol) and m-chloroperbenzoic acid (purity 69%, 39 g, 0.157 mol) in tetrahydrofuran (100 mL) was stirred with heating at 50° C. for 5 hr. The solvent was evaporated under reduced pressure, and the obtained residue was purified 3 times by silica gel column chromatography (NH silica gel, ethyl acetate) to give a white solid. The obtained solid was washed with ethyl acetate to give the title compound (24.7 g, 85%) as a white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was purified 3 times by silica gel column chromatography (NH silica gel, ethyl acetate)
  3. customto give a white solid
  4. washThe obtained solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-ed3e380e0be342cea3701031fcfb6d6b
Source dataset
uspto-grants-2013_05
Patent number
US08445509B2

Reaction notes

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