Реакция #167473

Уравнение реакции

tri(tert-butyl)phosphine

9-(3-bromophenyl)-10-phenylanthracene

9H-carbazole

sodium tert-butoxide

→

light-yellow solid

Выход 73.4%

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

Выход 73.4%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ДругоеInto a 200 mL three-neck flask were put
2. 2
   workup.ADDITIONwere added to this mixture
3. 3
   Другоеto be degassed while the pressure
4. 4
   workup.STIRRINGThis mixture was stirred under a nitrogen stream at 110° C. for 8 hours
5. 5
   ФильтрацияAfter the stirring, this mixture was subjected to suction filtration through Celite (Wako Pure Chemical Industries, Ltd., catalog No.: 531-16855), alumina, and Florisil (Wako Pure Chemical Industries, Ltd., catalog No.: 540-00135)
6. 6
   КонцентрированиеThe obtained filtrate was concentrated
7. 7
   Другоеto give a light-yellow oily substance
8. 8
   ДругоеThe obtained oily substance was recrystallized from toluene/hexane

Методика

Into a 200 mL three-neck flask were put 1.3 g (3.3 mmol) of 9-(3-bromophenyl)-10-phenylanthracene (abbr.: mPA), 0.55 g (3.3 mmol) of 9H-carbazole, and 0.63 g (6.6 mmol) of sodium tert-butoxide. After the air in the flask was replaced with nitrogen, 40 mL of toluene and 0.40 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to this mixture. This mixture was stirred to be degassed while the pressure was reduced. After the degassing, 95 mg (0.17 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred under a nitrogen stream at 110° C. for 8 hours. After the stirring, this mixture was subjected to suction filtration through Celite (Wako Pure Chemical Industries, Ltd., catalog No.: 531-16855), alumina, and Florisil (Wako Pure Chemical Industries, Ltd., catalog No.: 540-00135). The obtained filtrate was concentrated to give a light-yellow oily substance. The obtained oily substance was recrystallized from toluene/hexane to give 1.2 g of a light-yellow solid, which was the object of the synthesis, in a yield of 71%.

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