Reaktion #67886

Reaktionsgleichung

3-bromobiphenyl

1,4-dioxane

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

hydrazine hydrate

→

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

Lösungsmittel

water

ethyl acetate

water

methanol

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 40 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 3-bromobiphenyl (0.020 ml, 0.12 mmol) and 1,4-dioxane (1.5 ml), water (0.15 ml), potassium phosphate tribasic n-hydrate (170 mg, 0.72 mmol), sodium 1,3-dioxo-1,3-dihydro-isoindole-2-ylmethyl trifluoroborate (60 mg, 0.24 mmol), palladium(II) acetate (2.7 mg, 0.012 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (9.9 mg, 0.024 mmol) were added, and then the obtained reaction mixture was stirred at 94° C. (an outer temperature) overnight. The reaction mixture was cooled to room temperature, and then hydrazine hydrate (48 mg, 0.96 mmol) and methanol (2 ml) were added thereto, followed by heating to reflux for 40 min. The reaction mixture was cooled to room temperature, and then ethyl acetate and water 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 (ethyl acetate), thereby obtaining the entitled compound (11 mg, 51%) as the mixture with 2′-(dicyclohexyl-phosphinoyl)-2,6-dimethoxy-biphenyl (6.2 mg).

Quelle