반응 #92831

반응 방정식

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

수율 61.0%

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 4 hours under a nitrogen stream
4. 4
   여과After 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
   농축the filtrate was concentrated
6. 6
   기타to give a solid
7. 7
   기타The obtained solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1)
8. 8
   기타A suspension was formed by addition of toluene/hexane to the obtained solid
9. 9
   기타the suspension was irradiated with ultrasonic waves
10. 10
    여과Then, a solid was collected by suction filtration, so that 1.2 g of a yellow solid which
11. 11
    기타was obtained in a yield of 61%
12. 12
    기타The synthesis scheme of Step 2

실험 절차

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).

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