تفاعل #67885

معادلة التفاعل

2-bromoanisole

cesium carbonate

2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl

hydrazine hydrate

→

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

المردود 45.4%

المذيبات

water

1,4-dioxane

methanol

ethyl acetate

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر