反応 #487554

反応方程式

sodium carbonate

4-bromo-1-ethyl-2-nitrobenzene

4-chlorophenylboronic acid

→

4′-chloro-4-ethyl-3-nitrobiphenyl

収率 104.7%

溶媒

water

1,2-dimethoxyethane

反応条件

後処理

1. 1
   温度mixture is refluxed for 16 hours
2. 2
   温度The reaction mixture is cooled to room temperature
3. 3
   ろ過filtered through diatomaceous earth
4. 4
   洗浄washing with 200 ml of ethyl acetate
5. 5
   workup.ADDITIONThe mixture is poured into a separating funnel
6. 6
   その他the two phases are separated
7. 7
   抽出The aqueous phase is extracted with ethyl acetate
8. 8
   乾燥dried over anhydrous magnesium sulfate
9. 9
   ろ過filtered
10. 10
    その他the filtrate is evaporated in vacuo

実験手順

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.

出典