반응 #67884

반응 방정식

4-chlorobiphenyl

cesium carbonate

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

hydrazine hydrate

→

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

수율 55.7%

용매

water

1,4-dioxane

methanol

ethyl acetate

water

반응 조건

후처리

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

실험 절차

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).

출처