Phosphorus oxybromide → Ethyl 4-bromoquinoline-2-carboxylate

HRID 1497315Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497315
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1.P(Br)(Br)([Br:19])=O>C1(C)C=CC=CC=1.C(#N)C>[Br:19][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:3]=1

Komponenten

5

Edukt 2

HCID 24613Phosphorus oxybromideHCID 178469285HCID 178469285, Verbindung

Produkt 1

HCID 21992780Ethyl 4-bromoquinoline-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of ethyl 4-hydroxyquinoline-2-carboxylate (10.0 g, 46.0 mmol) and phosphorus oxybromide (13.2 g, 46.0 mmol) in 100 mL of toluene and 10.0 mL acetonitrile was heated at 75° C. for 1.5 h. The reaction mixture was cooled to room temperature, quenched slowly with water, and extracted with ethyl acetate. The organic fraction was washed with brine, dried over sodium sulfate, filtered, and concentrated. The resultant residue was subjected to silica gel chromatography eluting with 0-50% ethyl acetate in hexanes to afford ethyl 4-bromoquinoline-2-carboxylate that gave a mass ion (ES+) of 280.1 (79Br) for M+H+.

Aufarbeitung

  1. customquenched slowly with water
  2. extractionextracted with ethyl acetate
  3. washThe organic fraction was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluting with 0-50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-bf5239f09d5849a1858649a99f48d82b
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199939B2

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