Phosphorus oxychloride → 2,6-Dichloro-4-methylpyridine

HRID 37853

Reaktionsgleichung

Reaktionsgleichung von HRID 37853
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N+:3]=1[O-].P(Cl)(Cl)([Cl:12])=O>>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:12])[N:3]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 124874842-Chloro-4-methylpyridine 1-oxide

Produkt 1

HCID 108989972,6-Dichloro-4-methylpyridineAusbeute 43 %

Versuchsvorschrift

A mixture of 2-chloro-4-methyl-pyridine 1-oxide (1.0 g, 7.0 mmol) and phosphorus oxychloride (10 mL) was heated at reflux for 4 h. The volatiles were evaporated and the residue dissolved in ethyl acetate. The solution was washed with ice-water followed by sodium bicarbonate solution. The organic phase was again washed with water, brine solution, dried over anhydrous sodium sulfate and concentrated to obtain a residue which was purified by column chromatography over silica gel (60-120 mesh) using petroleum ether as eluent to afford 2,6-dichloro-4-methyl-pyridine (491 mg, 43%) as a white solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. customThe volatiles were evaporated
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThe solution was washed with ice-water
  6. washThe organic phase was again washed with water, brine solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customto obtain a residue which
  10. customwas purified by column chromatography over silica gel (60-120 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-51cb4aae7be0496d84ff01fb90662113
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524705B2

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