Реакция #92831

Уравнение реакции

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

Выход 61.0%

Растворители

hexane

toluene

Условия реакции

Обработка

1. 1
   ДругоеIn a 50-mL three-neck flask were put
2. 2
   ДругоеThis mixture was degassed
3. 3
   workup.STIRRINGThis mixture was stirred at 110° C. for 4 hours under a nitrogen stream
4. 4
   ФильтрацияAfter 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
   Концентрированиеthe filtrate was concentrated
6. 6
   Другоеto give a solid
7. 7
   ДругоеThe obtained solid was purified by silica gel column chromatography (developing solvent, hexane:toluene=5:1)
8. 8
   ДругоеA suspension was formed by addition of toluene/hexane to the obtained solid
9. 9
   Другоеthe suspension was irradiated with ultrasonic waves
10. 10
    ФильтрацияThen, a solid was collected by suction filtration, so that 1.2 g of a yellow solid which
11. 11
    Другоеwas obtained in a yield of 61%
12. 12
    ДругоеThe synthesis scheme of Step 2

Методика

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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