Dichloromethane → 6-Bromo-2,4-dichloro-3-phenylquinoline

Reaktionsgleichung

[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]1([CH:15]([C:19](O)=O)C(O)=O)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.P(Cl)(Cl)([Cl:24])=O.[CH2:27]([Cl:29])Cl>>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][CH:3]=1)[N:6]=[C:19]([Cl:24])[C:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[C:27]2[Cl:29]

Komponenten

Edukt 4

HCID 6344Dichloromethane

HCID 78074-Bromoaniline

HCID 24813Phosphorus oxychloride

HCID 75791Phenylmalonic acid

Produkt 1

HCID 867160576-Bromo-2,4-dichloro-3-phenylquinoline

Reaktionsbedingungen

Temperatur: 90 °C

Versuchsvorschrift

A mixture of 4-bromoaniline (10.0 g, 58.1 mmol), 2-phenylmalonic acid (11.0 g, 61.0 mmol), and phosphorus oxychloride (54.0 mL, 581 mmol) was heated in a 90° C. oil bath for 20 hours. The mixture was allowed to cool to room temperature and was diluted with CH2Cl2 in a large beaker (ca. 200 mL final volume). Ice (ca. 100 mL) was added and the mixture was stirred while monitoring the internal temperature; an ice bath was used to cool the mixture when the internal temperature reached 35° C. When the temperature of the mixture fell, the phases were separated and the aqueous phase was extracted once with CH2Cl2. The combined organic extracts were concentrated onto silica gel and the title compound was isolated by flash column chromatography (silica gel, 20-55% CH2Cl2-heptane).