Reaktion #159445

Reaktionsgleichung

3-(5-bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione

2,4-dichlorophenyl boronic acid

cesium fluoride

→

3-(2′,4′-dichloro-4-ethylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione

Lösungsmittel

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashing down any solids from the slides of the vial),
2. 2
   Sonstigeby purging with nitrogen
3. 3
   TemperaturThe mixture is heated at 160° C. under microwave irradiation for 15 minutes
4. 4
   Temperaturcooled to room temperature
5. 5
   Sonstigepartitioned between 2M hydrochloric acid and dichloromethane
6. 6
   SonstigeAfter separation of the organic layer the aqueous phase
7. 7
   Waschenis again washed with dichloromethane
8. 8
   Einengenconcentrated in vacuo
9. 9
   Sonstigeto afford a crude gum
10. 10
    SonstigeThis crude product is purified by flash column chromatography on silica gel (30% to 100% ethyl acetate/iso-hexane eluant ratio)

Vorschrift

To a microwave vial is added 3-(5-bromo-2-ethylphenyl)bicyclo[3.2.1]octane-2,4-dione (0.200 g, 0.623 mmol), 2,4-dichlorophenyl boronic acid (0.167 g, 0.87 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.040 g, 0.05 mmol) and cesium fluoride (0.284 g, 1.87 mmol). Degassed dimethoxyethane is next added (washing down any solids from the slides of the vial), followed by purging with nitrogen then stirring at room temperature for 5 minutes. The mixture is heated at 160° C. under microwave irradiation for 15 minutes, cooled to room temperature, then partitioned between 2M hydrochloric acid and dichloromethane. After separation of the organic layer the aqueous phase is again washed with dichloromethane, then all organic fractions are combined and concentrated in vacuo to afford a crude gum. This crude product is purified by flash column chromatography on silica gel (30% to 100% ethyl acetate/iso-hexane eluant ratio) to afford 3-(2′,4′-dichloro-4-ethylbiphen-3-yl)bicyclo[3.2.1]octane-2,4-dione.

Quelle