반응 #167474

반응 방정식

2-bromo-9,10-diphenylanthracene

9H-carbazole

sodium tert-butoxide

tri(tert-butyl)phosphine

→

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

수율 93.0%

용매

toluene

toluene

반응 조건

후처리

1. 1
   기타were put into a 100 mL three-neck flask
2. 2
   기타This mixture was degassed
3. 3
   온도After the reflux, this mixture was cooled to room temperature
4. 4
   여과The 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
   농축The obtained filtrate was concentrated
6. 6
   기타to give a light-brown oily substance
7. 7
   기타This oily substance was purified by silica gel column chromatography (a developing solvent
8. 8
   기타The obtained light-yellow solid substance was recrystallized from ethanol, so that 1.7 g of a light-yellow powdered solid
9. 9
   기타was obtained in a yield of 93%
10. 10
    온도was heated at 230° C. so as
11. 11
    기타purified (a train sublimation method)
12. 12
    기타After the sublimation purification, 1.5 g of a light-yellow solid substance
13. 13
    기타was recovered in a yield of 93%
14. 14
    기타A synthesis scheme of Step 1

실험 절차

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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