Diethyl Ether → Ethyl (6-bromo-2-nitropyridin-3-yloxy)acetate

HRID 639053Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639053
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[N:3]=1.C(=O)([O-])[O-:13].[K+].[K+].[CH3:18][CH2:19][O:20][CH2:21][CH3:22]>CC(C)=O.BrCC(OCC)=O>[CH2:19]([O:20][C:21](=[O:13])[CH2:22][O:8][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[N:3][C:2]([Br:1])=[CH:7][CH:6]=1)[CH3:18]

Komponenten

6

Edukt 3

HCID 3283Diethyl EtherHCID 11430Potassium CarbonateHCID 218738086-Bromo-2-nitropyridin-3-ol

Produkt 1

HCID 59560649Ethyl (6-bromo-2-nitropyridin-3-yloxy)acetateAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7748Ethyl bromoacetateKatalysatorHCID 180AcetoneLösungsmittel

Versuchsvorschrift

2-Bromo-5-hydroxy-6-nitropyridine (30 g, 0.14 mole) was suspended in acetone (200 ml), and potassium carbonate (39 g, 0.28 mole) was added, followed by ethyl bromoacetate (15.7 ml, 0.14 mmole). The reaction was heated at reflux for 10 hr, then was cooled to room temperature and diluted with Et2O. The precipitate was removed by suction filtration, and the filtrate was concentrated in vacuo to afford material (38 g, 89%), which was used without further purification; MS (ES) m/z 305.0 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 10 hr
  3. customThe precipitate was removed by suction filtration
  4. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d3e7e008c76d4b32a256040140b882b0
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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