تفاعل #67884

معادلة التفاعل

4-chlorobiphenyl

cesium carbonate

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

hydrazine hydrate

→

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

المردود 55.7%

المذيبات

water

1,4-dioxane

methanol

ethyl acetate

water

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwere added at room temperature
2. 2
   أخرىthe obtained reaction mixture
3. 3
   درجة الحرارةThe reaction mixture was cooled to room temperature
4. 4
   درجة الحرارةby heating
5. 5
   درجة الحرارةto reflux for 30 min
6. 6
   درجة الحرارةThe reaction mixture was cooled to room temperature
7. 7
   ترشيحfollowed by filtration with celite
8. 8
   أخرىThe organic layer of the filtrate was separated
9. 9
   غسيلwashed with saline
10. 10
    أخرىThe solvents were evaporated under reduced pressure from the organic layer
11. 11
    أخرىthe obtained residue was purified with NH-silica gel column chromatography (ethyl acetate)

الإجراء التجريبي

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).

المصدر