Dimethylformamide → 5-Bromo-2-chloro-3-nitropyridine

HRID 1485517

Reaktionsgleichung

Reaktionsgleichung von HRID 1485517
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=O)[NH:6][CH:7]=1.CN(C=O)C.O=P(Cl)(Cl)[Cl:19]>>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([Cl:19])=[N:6][CH:7]=1

Komponenten

4

Edukt 3

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 851475-Bromo-3-nitro-2-pyridone

Produkt 1

HCID 70194125-Bromo-2-chloro-3-nitropyridineAusbeute 85 %

Versuchsvorschrift

To a solution of 5-bromo-3-nitropyridin-2(1H)-one (4.62 g, 21.10 mmol) in POCl3 (46.2 ml) was added DMF (4.62 ml, 59.7 mmol) at room temperature. The mixture was refluxed for 2 hours, and then cooled to room temperature and concentrated in vacuo. The residue was treated with saturated aq. NaHCO3 and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:1) to give 5-bromo-2-chloro-3-nitropyridine (4.24 g, 85%) as a yellow solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 8.37 (1H, d, J=2.4 Hz), 8.70 (1H, d, J=2.0 Hz).

Aufarbeitung

  1. temperatureThe mixture was refluxed for 2 hours
  2. concentrationconcentrated in vacuo
  3. additionThe residue was treated with saturated aq. NaHCO3
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography on SiO2 (Hex:EtOAc=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-ac60d0e5e6884b69b696ccae93017adc
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422298B2

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