반응 #92830

반응 방정식

tri(tert-butyl)phosphine

9-(4-bromophenyl)-10-phenylanthracene

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

sodium tert-butoxide

→

pale yellow solid

수율 80.0%

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

수율 80.0%

용매

hexane

toluene

반응 조건

후처리

1. 1
   기타In a 50-mL three-neck flask were put
2. 2
   기타This mixture was degassed
3. 3
   workup.STIRRINGThis mixture was stirred at 110° C. for 6 hours under a nitrogen stream
4. 4
   추출After the stirring, the aqueous layer of this mixture was subjected to extraction with toluene
5. 5
   추출the solution of the extract
6. 6
   세척washed with saturated brine
7. 7
   건조The organic layer was dried over magnesium sulfate
8. 8
   여과This mixture was gravity-filtered
9. 9
   농축the filtrate was concentrated
10. 10
    기타to give a solid
11. 11
    기타The obtained solid was purified by silica gel column chromatography (
12. 12
    기타The obtained solid was recrystallized from toluene/hexane

실험 절차

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).

출처