Water → 6-Iodo-2-methoxy-3-[(4-methoxybenzyl)oxy]pyridine

HRID 70549

Reaktionsgleichung

Reaktionsgleichung von HRID 70549
[CH3:1][O-:2].[Na+].Br[C:5]1[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=[C:7]([I:21])[N:6]=1.O>CS(C)=O>[I:21][C:7]1[N:6]=[C:5]([O:2][CH3:1])[C:10]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 866580052-Bromo-6-iodo-3-[(4-methoxybenzyl)oxy]pyridine

Produkt 1

HCID 866580066-Iodo-2-methoxy-3-[(4-methoxybenzyl)oxy]pyridineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Sodium methoxide (11 g) was added to a solution of 2-bromo-6-iodo-3-[(4-methoxybenzyl)oxy]pyridine (17 g) in dimethyl sulfoxide (90 mL), and the mixture was stirred at 90° C. for three hours. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→70:30) to give 6-iodo-2-methoxy-3-[(4-methoxybenzyl)oxy]pyridine as a colorless powder (10 g, 71%).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=95:5→70:30)

Quellen und Nachweise

ORD-Eintrag
ord-123f671109544a23a689988da1088225
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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