Reaction #487554

Reaction equation

sodium carbonate

4-bromo-1-ethyl-2-nitrobenzene

4-chlorophenylboronic acid

→

4′-chloro-4-ethyl-3-nitrobiphenyl

Yield 104.7%

Solvents

water

1,2-dimethoxyethane

Conditions

Workup

1. 1
   Temperaturemixture is refluxed for 16 hours
2. 2
   TemperatureThe reaction mixture is cooled to room temperature
3. 3
   Filtrationfiltered through diatomaceous earth
4. 4
   Washwashing with 200 ml of ethyl acetate
5. 5
   workup.ADDITIONThe mixture is poured into a separating funnel
6. 6
   Otherthe two phases are separated
7. 7
   ExtractionThe aqueous phase is extracted with ethyl acetate
8. 8
   Dryingdried over anhydrous magnesium sulfate
9. 9
   Filtrationfiltered
10. 10
    Otherthe filtrate is evaporated in vacuo

Procedure

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.

Source