Reaktion #159484

Reaktionsgleichung

3-Bromo-4′-chloro-4-ethyl-2′-fluorobiphenyl

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

potassium phosphate

→

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigein degassed 1,2-(2.5 ml)
2. 2
   TemperaturThe mixture is cooled to room temperature
3. 3
   workup.ADDITIONdiluted with ethyl acetate
4. 4
   Waschenwashed with 2 M aqueous hydrochloric acid
5. 5
   WaschenThe organic phase is washed with brine
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe filtrate is evaporated under reduced pressure
9. 9
   Sonstigepurified by preparative reverse-phase HPLC
10. 10
    workup.ADDITIONFractions containing the desired product
11. 11
    Waschenwashed with brine
12. 12
    Trocknendried over anhydrous magnesium sulfate
13. 13
    Filtrationfiltered
14. 14
    Sonstigethe fitrate is evaporated under reduced pressure

Vorschrift

3-Bromo-4′-chloro-4-ethyl-2′-fluorobiphenyl (0.213 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), 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-(2.5 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. Fractions containing the desired product are taken up in ethyl acetate and washed with brine, dried over anhydrous magnesium sulfate, filtered and the fitrate is evaporated under reduced pressure to give 3-(4′-chloro-4-ethyl-2′-fluorobiphen-3-yl)-6,6-dimethylbicyclo[3.1.1]-heptane-2,4-dione.

Quelle