Reaktion #92831

Reaktionsgleichung

tri(tert-butyl)phosphine

2-(4-bromophenyl)-9,10-diphenylanthracene

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

sodium tert-butoxide

→

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

Ausbeute 61.0%

Lösungsmittel

hexane

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 50-mL three-neck flask were put
2. 2
   SonstigeThis mixture was degassed
3. 3
   workup.STIRRINGThis mixture was stirred at 110° C. for 4 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 solid
7. 7
   SonstigeThe obtained solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1)
8. 8
   SonstigeA suspension was formed by addition of toluene/hexane to the obtained solid
9. 9
   Sonstigethe suspension was irradiated with ultrasonic waves
10. 10
    FiltrationThen, a solid was collected by suction filtration, so that 1.2 g of a yellow solid which
11. 11
    Sonstigewas obtained in a yield of 61%
12. 12
    SonstigeThe synthesis scheme of Step 2

Vorschrift

In a 50-mL three-neck flask were put 1.3 g (2.7 mmol) of 2-(4-bromophenyl)-9,10-diphenylanthracene, 0.93 g (2.7 mmol) of 3-(dibenzothiophen-4-yl)-9H-carbazole, and 0.76 g (8.0 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, 76 mg (0.13 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 4 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), and the filtrate was concentrated to give a solid. The obtained solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1). A suspension was formed by addition of toluene/hexane to the obtained solid, and the suspension was irradiated with ultrasonic waves. Then, a solid was collected by suction filtration, so that 1.2 g of a yellow solid which was the object of the synthesis was obtained in a yield of 61%. The synthesis scheme of Step 2 is illustrated in (b-12).

Quelle