Reaktion #92830

Reaktionsgleichung

tri(tert-butyl)phosphine

9-(4-bromophenyl)-10-phenylanthracene

3-(6-phenyldibenzothiophen-4-yl)-9H-carbazole

sodium tert-butoxide

→

pale yellow solid

Ausbeute 80.0%

3-(6-Phenyldibenzothiophen-4-yl)-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole

Ausbeute 80.0%

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 6 hours under a nitrogen stream
4. 4
   ExtraktionAfter the stirring, the aqueous layer of this mixture was subjected to extraction with toluene
5. 5
   Extraktionthe solution of the extract
6. 6
   Waschenwashed with saturated brine
7. 7
   TrocknenThe organic layer was dried over magnesium sulfate
8. 8
   FiltrationThis mixture was gravity-filtered
9. 9
   Einengenthe filtrate was concentrated
10. 10
    Sonstigeto give a solid
11. 11
    SonstigeThe obtained solid was purified by silica gel column chromatography (
12. 12
    SonstigeThe obtained solid was recrystallized from toluene/hexane

Vorschrift

In a 50-mL three-neck flask were put 1.3 g (3.3 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 1.0 g (2.4 mmol) of 3-(6-phenyldibenzothiophen-4-yl)-9H-carbazole, and 0.95 g (9.9 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, 11 mg (0.18 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 6 hours under a nitrogen stream. After the stirring, the aqueous layer of this mixture was subjected to extraction with toluene, and the solution of the extract and the organic layer were combined and washed with saturated brine. The organic layer was dried over magnesium sulfate. This mixture was gravity-filtered, and the filtrate was concentrated to give a solid. The obtained solid was purified by silica gel column chromatography (developing solvent, toluene:hexane=1:9 and then toluene:hexane=3:7). The obtained solid was recrystallized from toluene/hexane to give 1.4 g of a pale yellow solid which was the object of the synthesis in a yield of 80%. The synthesis scheme of Step 2 is illustrated in (b-11).

Quelle