Methyl iodide → 3-Bromo-2-chloro-5-methoxypyridine

HRID 473743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473743
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[N:6][C:7]=1[Cl:8].[C:10](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.O>[Br:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[C:4]([O:9][CH3:10])[CH:3]=1

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 145952265-Bromo-6-chloropyridin-3-ol

Produkt 1

HCID 467388143-Bromo-2-chloro-5-methoxypyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a stirred mixture of 5-bromo-6-chloropyridin-3-ol (2.95 g, 14.15 mmol) and potassium carbonate (1.28 mL, 21.23 mmol) in acetonitrile (45 mL) under a nitrogen atmosphere was added iodomethane (0.93 mL, 14.86 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to give 3-bromo-2-chloro-5-methoxypyridine. MS (ESI, pos. ion) m/z: 221.9 and 223.9 (M+1).

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with sat. sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-955f172ddda64ad9983685d692155e5b
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637500B2

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