Phosphorus oxybromide → 2-Bromo-6-methoxyquinoline

HRID 2045715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2045715
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[CH:6]2.P(Br)(Br)([Br:16])=O>>[Br:16][C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Komponenten

3

Edukt 2

HCID 24613Phosphorus oxybromideHCID 2282682-Hydroxy-6-methoxyquinoline

Produkt 1

HCID 114704222-Bromo-6-methoxyquinolineAusbeute 49,3 %

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

6-Methoxyquinolin-2(1H)-one (6.81 g, 38.9 mmol) was carefully added to POBr3 (18.9 g, 66.1 mmol) at 60° C., and the resulting solution was stirred at 140° C. for 2.5 h. The reaction mixture was cooled and poured onto crushed ice, and the solid was collected by filtration. Purification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether) afforded the title compound (4.57 g, 49.3%) as a solid. LCMS (ES+) m/z 238, 240 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. additionpoured
  3. customonto crushed ice
  4. filtrationthe solid was collected by filtration
  5. customPurification of this material on silica gel (gradient elution from 5 to 12% EtOAc in petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-9042e30c9dd44a0ea7cfddb3ec75d3e9
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591878B2

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