반응 #92825

반응 방정식

2-iodo-9,10-diphenylanthracene

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

sodium tert-butoxide

tri(tert-butyl)phosphine

→

3-(dibenzothiophen-4-yl)-9-(9,10-diphenyl-2-anthryl)-9H-carbazole

수율 76.0%

용매

hexane

toluene

반응 조건

후처리

1. 1
   기타This mixture was degassed
2. 2
   workup.STIRRINGThis mixture was stirred at 110° C. for 4 hours under a nitrogen stream
3. 3
   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)
4. 4
   농축The filtrate was concentrated
5. 5
   기타to give a yellow solid
6. 6
   기타The obtained solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1)
7. 7
   농축The obtained fraction was concentrated
8. 8
   기타to give a yellow solid
9. 9
   기타The obtained yellow solid was recrystallized from toluene/hexane, so that 1.5 g of a yellow solid
10. 10
    기타was obtained in 76% yield
11. 11
    기타The synthesis scheme of Step 2

실험 절차

To a 100-mL three-neck flask were added 1.4 g (3.0 mmol) of 2-iodo-9,10-diphenylanthracene, 1.1 g (3.0 mmol) of 3-(dibenzothiophen-4-yl)-9H-carbazole, and 0.86 g (9.0 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, 86 mg (0.15 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the 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). The filtrate was concentrated to give a yellow solid. The obtained solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1). The obtained fraction was concentrated to give a yellow solid. The obtained yellow solid was recrystallized from toluene/hexane, so that 1.5 g of a yellow solid was obtained in 76% yield. The synthesis scheme of Step 2 is illustrated in (b-7).

출처