Phosphorus oxychloride → Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate

HRID 2060612Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2060612
[Cl:1][CH2:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:5]1[N:4]=[C:3]([CH2:2][Cl:1])[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 582166522-(Chloromethyl)-3-(methoxycarbonyl)pyridine 1-oxide

Produkt 1

HCID 59525762Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate

Versuchsvorschrift

Methyl 2-(chloromethyl)pyridine-3-carboxylate 1-oxide (17.85 g, 89 mmol) was stirred in refluxing POCl3 (80 mL, 858 mmol) for 3 hours. Room temperature was attained and the reaction mixture poured into ice-water. The resulting beige precipitate was collected by filtration and purified by flash chromatography (silica, 2-20% ethyl acetate/hexanes) to afford the title compound as a white solid. 1H NMR (CDCl3, 600 MHz) δ 8.22 (d, 1H), 7.37 (d, 1H), 5.03 (s, 2H), 3.95 (s, 3H).

Aufarbeitung

  1. customRoom temperature
  2. filtrationThe resulting beige precipitate was collected by filtration
  3. custompurified by flash chromatography (silica, 2-20% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ebb264b40ad342e0b4069dfdc1d873f6
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278335B2

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