Reaktion #67884

Reaktionsgleichung

4-chlorobiphenyl

cesium carbonate

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

hydrazine hydrate

→

2′-(dicyclohexyl-phosphinoyl)-2,6-dimethoxy-biphenyl

Ausbeute 55.7%

Lösungsmittel

water

1,4-dioxane

methanol

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   Sonstigethe obtained reaction mixture
3. 3
   TemperaturThe reaction mixture was cooled to room temperature
4. 4
   Temperaturby heating
5. 5
   Temperaturto reflux for 30 min
6. 6
   TemperaturThe reaction mixture was cooled to room temperature
7. 7
   Filtrationfollowed by filtration with celite
8. 8
   SonstigeThe organic layer of the filtrate was separated
9. 9
   Waschenwashed with saline
10. 10
    SonstigeThe solvents were evaporated under reduced pressure from the organic layer
11. 11
    Sonstigethe obtained residue was purified with NH-silica gel column chromatography (ethyl acetate)

Vorschrift

To the mixture of 4-chlorobiphenyl (15 mg, 0.079 mmol) and 1,4-dioxane (1 ml), water (0.1 ml), cesium carbonate (0.16 g, 0.48 mmol), sodium 1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl trifluoroborate (40 mg, 0.16 mmol), palladium(II) acetate (1.8 mg, 0.0079 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (6.5 mg, 0.016 mmol) were added at room temperature, and then the obtained reaction mixture was stirred at 100° C. (an outer temperature) overnight. The reaction mixture was cooled to room temperature, and then hydrazine hydrate (40 mg, 0.79 mmol) and methanol (2 ml) were added thereto, followed by heating to reflux for 30 min. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added thereto, followed by filtration with celite. The organic layer of the filtrate was separated and washed with saline. The solvents were evaporated under reduced pressure from the organic layer, and then the obtained residue was purified with NH-silica gel column chromatography (ethyl acetate), thereby obtaining the entitled compound (7.7 mg, 53%) as the mixture with 2′-(dicyclohexyl-phosphinoyl)-2,6-dimethoxy-biphenyl (3.8 mg).

Quelle