Hydrochloric Acid → (6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

HRID 1054911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1054911
[Br:1][C:2]1[N:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([OH:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][O:19][C:20](=[O:23])[CH2:21]Br.Cl>CS(C)=O>[CH3:18][O:19][C:20](=[O:23])[CH2:21][O:11][C:5]1[C:6]([N+:8]([O-:10])=[O:9])=[N:7][C:2]([Br:1])=[CH:3][CH:4]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 218738086-Bromo-2-nitropyridin-3-ol

Produkt 1

HCID 90011186(6-Bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

6-Bromo-2-nitropyridin-3-ol (10.8 g, 49.1 mmol) was dissolved in dimethylsulfoxide (DMSO) (30 mL). Potassium carbonate (13.6 g, 98.6 mmol) and bromoacetic acid methyl ester (7.0 mL, 74 mmol) were added and the reaction mixture was stirred at 60° C. for two hours. Then, the reaction mixture was cooled to room temperature and neutralized with 1N HCl(aq). The aqueous solution was extracted twice with ethyl acetate, and the combined organic extracts were washed with brine. The product was purified by column chromatography (SiO2, EtOAc/hexanes) to afford (6-bromo-2-nitropyridin-3-yloxy)acetic acid methyl ester. Yield 10.9 g (37.5 mmol, 76%). LCMS (ESI): calc. C8H7BrN2O5=290, 292; obs. Low ionization.

Aufarbeitung

  1. extractionThe aqueous solution was extracted twice with ethyl acetate
  2. washthe combined organic extracts were washed with brine
  3. customThe product was purified by column chromatography (SiO2, EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-c7694631f8a24b94987eda083d4570fd
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09394315B2

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