Reaktion #67885

Reaktionsgleichung

2-bromoanisole

cesium carbonate

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

hydrazine hydrate

→

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

Ausbeute 45.4%

Lösungsmittel

water

1,4-dioxane

methanol

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
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 1 hour
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 (heptane:ethyl acetate=1:4)

Vorschrift

To the mixture of 2-bromoanisole (0.020 ml, 0.16 mmol) and 1,4-dioxane (2 ml), water (0.2 ml), cesium carbonate (0.32 g, 0.97 mmol), sodium 1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl trifluoroborate (81 mg, 0.32 mmol), palladium(II) acetate (3.6 mg, 0.016 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (13 mg, 0.032 mmol) were added, and then the obtained reaction mixture was stirred at 95° C. (an outer temperature) overnight. The reaction mixture was cooled to room temperature, and then hydrazine hydrate (0.039 ml, 0.81 mmol) and methanol (2 ml) were added thereto, followed by heating to reflux for 1 hour. The reaction mixture was cooled to room temperature, and then water and ethyl acetate were added to the reaction mixture, 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 (heptane:ethyl acetate=1:4), thereby obtaining the entitled compound (4.1 mg, 19%) as the mixture with 2′-(dicyclohexyl-phosphinoyl)-2,6-dimethoxy-biphenyl (6.2 mg).

Quelle