반응 #955972

반응 방정식

4-aminobiphenyl

4-bromo-1,1′:3′,1″-terphenyl

sodium tert-butoxide

→

white solid

수율 74.3%

N-([1,1′-biphenyl]-4-yl)-[1,1′:3′,1″-terphenyl]-4-amine

수율 74.3%

용매

toluene

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONThe catalyst solution was added to the reaction mixture
2. 2
   workup.STIRRINGstirred for 2 minutes
3. 3
   기타Flask was capped
4. 4
   workup.WAITleft
5. 5
   workup.STIRRINGto stir in the drybox overnight at room temperature
6. 6
   기타Next day, reaction mixture
7. 7
   여과filtered through a one-inch plug of silica gel
8. 8
   세척washing with 500 ml of dichloromethane
9. 9
   기타Removal of volatiles under reduced pressure
10. 10
    기타gave a yellow solid
11. 11
    기타Crude product was purified by trituration with diethyl ether

실험 절차

In a drybox, 4-aminobiphenyl (0.542 g) and 4-bromo-1,1′:3′,1″-terphenyl (0.89 g) were combined in a round-bottom flask and dissolved in 10 ml of dry toluene. Tris(tert-butyl)phosphine (0.022 g, 0.11 mmol) and tris(dibenzylideneacetone) dipalladium(0) (0.05 g, 0.055 mmol) were dissolved in 10 ml of dry toluene and stirred for 5 minutes. The catalyst solution was added to the reaction mixture, stirred for 2 minutes and was followed by sodium tert-butoxide (0.32 g, 3.3 mmol). Flask was capped and left to stir in the drybox overnight at room temperature. Next day, reaction mixture was taken out of the box and filtered through a one-inch plug of silica gel topped with celite, washing with 500 ml of dichloromethane. Removal of volatiles under reduced pressure gave a yellow solid. Crude product was purified by trituration with diethyl ether to give 0.85 g (73%) of a white solid. Structure was confirmed by 1H NMR spectroscopy.

출처