Reacción #487554

Ecuación de reacción

sodium carbonate

4-bromo-1-ethyl-2-nitrobenzene

4-chlorophenylboronic acid

→

4′-chloro-4-ethyl-3-nitrobiphenyl

Rendimiento 104.7%

Disolventes

water

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturamixture is refluxed for 16 hours
2. 2
   TemperaturaThe reaction mixture is cooled to room temperature
3. 3
   Filtraciónfiltered through diatomaceous earth
4. 4
   Lavadowashing with 200 ml of ethyl acetate
5. 5
   workup.ADDITIONThe mixture is poured into a separating funnel
6. 6
   Otrothe two phases are separated
7. 7
   ExtracciónThe aqueous phase is extracted with ethyl acetate
8. 8
   Secadodried over anhydrous magnesium sulfate
9. 9
   Filtraciónfiltered
10. 10
    Otrothe filtrate is evaporated in vacuo

Procedimiento

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.

Fuente