반응 #92827

반응 방정식

tri(tert-butyl)phosphine

9-(3-bromophenyl)-10-phenylanthracene

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

sodium tert-butoxide

→

pale yellow solid

수율 73.8%

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

수율 73.8%

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 5 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 yellow solid
7. 7
   기타The obtained solid was recrystallized from toluene
8. 8
   기타The obtained crystal was purified by high performance liquid column chromatography (abbreviation: HPLC) (developing solvent: chloroform)
9. 9
   농축The obtained fraction was concentrated

실험 절차

In a 50-mL three-neck flask were put 1.2 g (3.0 mmol) of 9-(3-bromophenyl)-10-phenylanthracene, 1.1 g (3.0 mmol) of 3-(dibenzothiophen-4-yl)-9H-carbazole, and 0.87 g (9.1 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, 87 mg (0.15 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 5 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 recrystallized from toluene. The obtained crystal was purified by high performance liquid column chromatography (abbreviation: HPLC) (developing solvent: chloroform). The obtained fraction was concentrated to give 1.5 g of a pale yellow solid in 72% yield. The synthesis scheme of Step 2 is illustrated in (b-9).

출처