Water → 2-Bromo-6-iodo-3-methoxypyridine

HRID 604213

Reaktionsgleichung

Reaktionsgleichung von HRID 604213
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].CI.O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([O:8][CH3:10])=[CH:6][CH:5]=[C:4]([I:9])[N:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 109794792-Bromo-6-iodopyridin-3-ol

Produkt 1

HCID 110990402-Bromo-6-iodo-3-methoxypyridineAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-Bromo-6-iodo-pyridin-3-ol (2.98 g) is dissolved in N,N-dimethylformamide (140 ml) and thereto are added cesium carbonate (16.3 g) and methyl iodide (1.25 mL) and the mixture is stirred at room temperature overnight. To the reaction solution are added water and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1) to give 2-bromo-6-iodo-3-methoxy-pyridine (2.45 g). MS (m/z): 314/316 [M+H]+

Aufarbeitung

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=19:1→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-f29a74ca54a14148937e15707662d584
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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