Chloromethyl Methyl Ether → 2-Bromo-5-(methoxymethoxy)pyridine

HRID 1009107

Reaktionsgleichung

Reaktionsgleichung von HRID 1009107
[Br:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[H-].[Na+].Cl[CH2:12][O:13][CH3:14].C(=O)(O)[O-].[Na+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:12][O:13][CH3:14])=[CH:6][N:7]=1

Komponenten

6

Edukt 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 27628652-Bromo-5-hydroxypyridine

Produkt 1

HCID 574336662-Bromo-5-(methoxymethoxy)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 6-bromopyridin-3-ol (25 g, 144 mmol) in DMF (300 mL) at 0° C. under N2 is added portionwise NaH (5.7 g, 144 mmol) over 5 min. The reaction was stirred 1 h, then chloro(methoxy)methane (12 g, 144 mmol) was added and the reaction stirred an additional 1 h at 0° C. Saturated sodium bicarbonate (500 mL) was added slowly and the suspension stirred 30 min and warmed to rt. The solution was extracted with EtOAc (3×400 mL), the combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL), dried (Na2SO4), and concentrated in vacuo to give the title compound as a brown oil.

Aufarbeitung

  1. stirringthe reaction stirred an additional 1 h at 0° C
  2. stirringthe suspension stirred 30 min
  3. extractionThe solution was extracted with EtOAc (3×400 mL)
  4. washthe combined organic layers washed with H2O (500 mL), saturated NaCl (500 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-7e6ee0ae993f4209b6cb461513c40d58
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973047B2

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