Methyl iodide → 2-Bromo-3-methoxy-6-methylpyridine

HRID 488814

Reaktionsgleichung

Reaktionsgleichung von HRID 488814
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1.[C:10](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([CH3:9])[N:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 119591012-Bromo-6-methylpyridin-3-ol

Produkt 1

HCID 109655632-Bromo-3-methoxy-6-methylpyridineAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A stirred mixture of 2-bromo-3-hydroxy-6-methyl-pyridine (7.89 g, 42.0 mmol), potassium carbonate (11.60 g, 83.9 mmol) and iodomethane (8.93 g, 62.9 mmol, 3.92 mL) in acetone (100 mL) was heated under reflux overnight. The mixture was filtered, evaporated and purified on silica gel (hexane:ethyl acetate, 95:5 to 9:1) to give the desired product as a white solid (7.49 g, 88.3%). 1H NMR (500 MHz, CDCl3): δ 2.46 (s, 3 H), 3.87 (s, 3 H), 7.04 (s, 2 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. filtrationThe mixture was filtered
  4. customevaporated
  5. custompurified on silica gel (hexane:ethyl acetate, 95:5 to 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-58635002450b4ed6aaeee81ac6a86c27
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974826B2

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