Реакция #487554

Уравнение реакции

sodium carbonate

4-bromo-1-ethyl-2-nitrobenzene

4-chlorophenylboronic acid

→

4′-chloro-4-ethyl-3-nitrobiphenyl

Выход 104.7%

Растворители

water

1,2-dimethoxyethane

Условия реакции

Обработка

1. 1
   Температураmixture is refluxed for 16 hours
2. 2
   ТемператураThe reaction mixture is cooled to room temperature
3. 3
   Фильтрацияfiltered through diatomaceous earth
4. 4
   Промывкаwashing with 200 ml of ethyl acetate
5. 5
   workup.ADDITIONThe mixture is poured into a separating funnel
6. 6
   Другоеthe two phases are separated
7. 7
   ЭкстракцияThe aqueous phase is extracted with ethyl acetate
8. 8
   Сушкаdried over anhydrous magnesium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    Другоеthe filtrate is evaporated in vacuo

Методика

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.

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