반응 #487554

반응 방정식

sodium carbonate

4-bromo-1-ethyl-2-nitrobenzene

4-chlorophenylboronic acid

→

4′-chloro-4-ethyl-3-nitrobiphenyl

수율 104.7%

용매

water

1,2-dimethoxyethane

반응 조건

후처리

1. 1
   온도mixture is refluxed for 16 hours
2. 2
   온도The reaction mixture is cooled to room temperature
3. 3
   여과filtered through diatomaceous earth
4. 4
   세척washing with 200 ml of ethyl acetate
5. 5
   workup.ADDITIONThe mixture is poured into a separating funnel
6. 6
   기타the two phases are separated
7. 7
   추출The aqueous phase is extracted with ethyl acetate
8. 8
   건조dried over anhydrous magnesium sulfate
9. 9
   여과filtered
10. 10
    기타the filtrate is evaporated in vacuo

실험 절차

To 4-bromo-1-ethyl-2-nitrobenzene (20.0 g, 0.087 mol) in 150 ml 1,2-dimethoxyethane is added, at room temperature, 4-chlorophenylboronic acid (14.98 g, 0.096 mol) and tetrakis(triphenylphosphine)palladium(0) (2.0 g, 0.00174 mol) and nitrogen gas is bubbled through the mixture. After stirring for 10 minutes at 20° C., a solution of sodium carbonate (73.8 g, 0.696 mol) in water (350 ml) is added and mixture is refluxed for 16 hours. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth, washing with 200 ml of ethyl acetate. The mixture is poured into a separating funnel and the two phases are separated. The aqueous phase is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo to give 4′-chloro-4-ethyl-3-nitrobiphenyl (23.84 g) as a brown oil used without further purification in the next step.

출처