Ethyl Glycolate → Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetate

HRID 1360295Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360295
[H-].[Na+].[C:3]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:4][OH:5].[Br:10][C:11]1[CH:12]=[C:13]([N+:18]([O-:20])=[O:19])[C:14](Cl)=[N:15][CH:16]=1.C(=O)([O-])O.[Na+]>O1CCOCC1>[CH2:8]([O:7][C:3](=[O:6])[CH2:4][O:5][C:14]1[C:13]([N+:18]([O-:20])=[O:19])=[CH:12][C:11]([Br:10])=[CH:16][N:15]=1)[CH3:9]

Komponenten

6

Edukt 4

HCID 12184Ethyl GlycolateHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 70194125-Bromo-2-chloro-3-nitropyridine

Produkt 1

HCID 4647502Ethyl 2-((5-bromo-3-nitropyridin-2-yl)oxy)acetateAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Sodium hydride (55% dispersion in mineral oil, 603 mg, 13.8 mmol) was added to a solution of ethyl glycolate (1.43 g, 13.8 mmol) in 1,4-dioxane, and the reaction mixture was heated at 70° C. for 1 h, then 5-bromo-2-chloro-3-nitropyridine (Eur. Pat. Appl. EP 122109 (1984); 1.64 g, 6.91 mmol) was added, and stirring was continued at 70° C. for 1 h and at room temperature for 16 h. The reaction mixture was then neutralized with sat. aq. sodium hydrogencarbonate solution and extracted three times with dichloromethane. The organic layers were pooled, dried (Na2SO4), and evaporated. Chromatography (SiO2, hexane-ethyl acetate gradient) furnished (5-bromo-3-nitropyridin-2-yloxy)-acetic acid ethyl ester (1.03 g, 49%). Light yellow liquid, MS (ISP)=305.1 (M+H)+.

Aufarbeitung

  1. extractionextracted three times with dichloromethane
  2. dry with materialdried (Na2SO4)
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-04254191ba3f4b3795b2169ef2469748
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879845B2

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