Reaktion #92832

Reaktionsgleichung

tri(tert-butyl)phosphine

2-(3-bromophenyl)-9,10-diphenylanthracene

3-(dibenzothiophen-4-yl)-9H-carbazole

sodium tert-butoxide

→

yellow solid

Ausbeute 70.0%

3-(Dibenzothiophen-4-yl)-9-[3-(9,10-diphenyl-2-anthryl)phenyl]-9H-carbazole

Ausbeute 70.0%

Lösungsmittel

hexane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 100-mL three-neck flask were put
2. 2
   SonstigeThis mixture was degassed
3. 3
   workup.STIRRINGThis mixture was stirred at 110° C. for 5 hours under a nitrogen stream
4. 4
   FiltrationAfter the stirring, the obtained mixture was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
5. 5
   EinengenThe filtrate was concentrated
6. 6
   Sonstigeto give a yellow solid
7. 7
   SonstigeThis solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1)
8. 8
   SonstigeThe obtained solid was recrystallized from toluene/hexane

Vorschrift

In a 100-mL three-neck flask were put 1.0 g (2.1 mmol) of 2-(3-bromophenyl)-9,10-diphenylanthracene, 0.72 g (2.1 mmol) of 3-(dibenzothiophen-4-yl)-9H-carbazole, and 0.59 g (6.2 mmol) of sodium tert-butoxide. After the air in the flask was replaced with nitrogen, to this mixture were added 20 mL of toluene and 0.2 mL of tri(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was degassed by being stirred while the pressure was reduced. After the degassing, 59 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 5 hours under a nitrogen stream. After the stirring, the obtained mixture was suction-filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), alumina, and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). The filtrate was concentrated to give a yellow solid. This solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1). The obtained solid was recrystallized from toluene/hexane to give 1.1 g of a yellow solid in 70% yield. The synthesis scheme of Step 2 is illustrated in (b-14).

Quelle