Reaktion #68758

Reaktionsgleichung

2-(5-bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

2,4-dichlorophenylboronic acid

cesium fluoride

→

2-(2′,4′-dichloro-4-cyclopropylbiphenyl-3-yl)-cyclopentane-1,3-dione

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter evacuating
2. 2
   Sonstigeflushing with nitrogen (×3) the mixture
3. 3
   ExtraktionAfter dilution with distilled water the crude product is extracted with ethyl acetate (×3)
4. 4
   Waschenthe organic phase is washed with brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   SonstigeThe crude product is then purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant)
8. 8
   Sonstigefurther triturated with hexanes

Vorschrift

To a mixture of 2-(5-bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione (0.100 g, 0.34 mmol), 2,4-dichlorophenylboronic acid (0.090 g, 0.47 mmol), [1,1′-bis(diphenylphosphino)-ferrocene]palladium(II)chloride (22 mg, 0.027 mmol) and cesium fluoride (0.152 g, 1.0 mmol) is added 1,2-dimethoxyethane (1 ml). After evacuating and flushing with nitrogen (×3) the mixture is heated at 160° C. for 15 minutes under microwave irradiation. After dilution with distilled water the crude product is extracted with ethyl acetate (×3), and the organic phase is washed with brine, dried over magnesium sulfate and concentrated in vacuo. The crude product is then purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant) and further triturated with hexanes to afford 2-(2′,4′-dichloro-4-cyclopropylbiphenyl-3-yl)-cyclopentane-1,3-dione as a white powder.

Quelle