反応 #167474

反応方程式

2-bromo-9,10-diphenylanthracene

9H-carbazole

sodium tert-butoxide

tri(tert-butyl)phosphine

→

9-(9,10-diphenyl-2-anthryl)-9H-carbazole

収率 93.0%

溶媒

toluene

toluene

反応条件

後処理

1. 1
   その他were put into a 100 mL three-neck flask
2. 2
   その他This mixture was degassed
3. 3
   温度After the reflux, this mixture was cooled to room temperature
4. 4
   ろ過The mixture was then filtered through alumina, Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
5. 5
   濃縮The obtained filtrate was concentrated
6. 6
   その他to give a light-brown oily substance
7. 7
   その他This oily substance was purified by silica gel column chromatography (a developing solvent
8. 8
   その他The obtained light-yellow solid substance was recrystallized from ethanol, so that 1.7 g of a light-yellow powdered solid
9. 9
   その他was obtained in a yield of 93%
10. 10
    温度was heated at 230° C. so as
11. 11
    その他purified (a train sublimation method)
12. 12
    その他After the sublimation purification, 1.5 g of a light-yellow solid substance
13. 13
    その他was recovered in a yield of 93%
14. 14
    その他A synthesis scheme of Step 1

実験手順

First, 1.5 g (3.7 mmol) of 2-bromo-9,10-diphenylanthracene, which was used in Step 1 of Synthesis Example 5, 610 mg (3.7 mmol) of 9H-carbazole, and 1.5 g (16 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the air in the flask was replaced with nitrogen. 20 mL of toluene and 0.10 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to this mixture. This mixture was degassed while being stirred under reduced pressure, and after the degassing, 58 mg (0.10 mmol) of bis(dibenzylideneacetone)palladium(0) was added. This mixture was refluxed at 110° C. for 5 hours. After the reflux, this mixture was cooled to room temperature and about 20 mL of toluene was added to this mixture. The mixture was then filtered through alumina, Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). The obtained filtrate was concentrated to give a light-brown oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was a mixed solvent of hexane:toluene=6:4). The obtained light-yellow solid substance was recrystallized from ethanol, so that 1.7 g of a light-yellow powdered solid was obtained in a yield of 93%. At a pressure of 8.7 Pa and with an argon gas flowing at a flow rate of 3.0 mL/min, 1.6 g of the obtained light-yellow powdered solid substance was heated at 230° C. so as to be sublimated and purified (a train sublimation method). After the sublimation purification, 1.5 g of a light-yellow solid substance was recovered in a yield of 93%. A synthesis scheme of Step 1 is shown in (F-3) given below.

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