Reaktion #159481

Reaktionsgleichung

3-Bromo-4′-chloro-4-ethylbiphenyl

6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione

potassium phosphate

→

3-(4′-chloro-4-ethylbiphen-3-yl)-6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione

Lösungsmittel

ethyl acetate

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeprepared by the method of W
2. 2
   TemperaturThe mixture is cooled to room temperature
3. 3
   Waschenwashed with 2 M aqueous hydrochloric acid
4. 4
   WaschenThe organic phase is washed with brine
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe filtrate is evaporated under reduced pressure
8. 8
   Sonstigepurified by preparative reverse-phase HPLC

Vorschrift

3-Bromo-4′-chloro-4-ethylbiphenyl (0.200 g, 0.68 mmol) is added to a mixture of 6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione (0.124 g, 0.81 mmol), prepared by the method of W. Childers et al., US2006/0004108, powdered potassium phosphate (0.316 g, 1.49 mmol), palladium (II) acetate (0.008 g, 0.034 mmol) and (2-dicyclohexylphosphino)-2′,4′,6′-triisopropylbiphenyl (0.024 g, 0.051 mmol) in degassed 1,2-dimethoxyethane (2 ml) and the mixture is stirred and heated to 160° C. for 1 hour under microwave irradiation. The mixture is cooled to room temperature, diluted with ethyl acetate and washed with 2 M aqueous hydrochloric acid. The organic phase is washed with brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is taken up in N,N-dimethylformamide (2 ml) and purified by preparative reverse-phase HPLC to give 3-(4′-chloro-4-ethylbiphen-3-yl)-6,6-dimethylbicyclo[3.1.1]heptane-2,4-dione.

Quelle