Phosphorus oxychloride → 7-Bromo-2-chloroquinoxaline

HRID 524370

Reaktionsgleichung

Reaktionsgleichung von HRID 524370
O=P(Cl)(Cl)[Cl:3].[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([N:11]=[CH:12][C:13](=O)[NH:14]2)=[CH:9][CH:8]=1>CN(C=O)C>[Cl:3][C:13]1[CH:12]=[N:11][C:10]2[C:15](=[CH:16][C:7]([Br:6])=[CH:8][CH:9]=2)[N:14]=1

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 49132647-bromo-1H-quinoxalin-2-one

Produkt 1

HCID 49132537-Bromo-2-chloroquinoxalineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

300 mL POCl3 and 1 mL DMF were added to 7-bromo-1H-quinoxalin-2-one (30 g, 133.0 mmol) under stirring. The mixture was heated to reflux over a period of 1 h and refluxed for 2 h. After cooling to rt, the mixture was slowly poured onto 1 kg crushed ice. After 1 h, the solid was filtered and the precipitate was washed with water and dried. The dry product was washed with 100 mL ethyl acetate/petrol ether (1:9) to yield 27 g (83%) of a brownish solid: 1H-NMR (300 MHz, CDCl3): δ=8.78 (1H, s), 8.21 (1H, s) 7.98 (1H, d), 7.83 (1H, d), ppm. UPLC-MS: RT=1.28 min; m/z (ES+) 243.5 [MH+]; required MW=242.5. Mp. 145° C.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux over a period of 1 h
  3. temperaturerefluxed for 2 h
  4. additionthe mixture was slowly poured onto 1 kg
  5. customcrushed ice
  6. filtrationthe solid was filtered
  7. washthe precipitate was washed with water
  8. customdried
  9. washThe dry product was washed with 100 mL ethyl acetate/petrol ether (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-7c605cbafcaf48efa576739e0f5ec8e7
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340528B2

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