反応 #975868

反応方程式

dimethoxyethanol

potassium carbonate

3-bromocarbazole

N-phenylcarbazol-3-boronic acid

→

white solid

収率 80.8%

9-phenyl-3,3′-bi(9H-carbazole)

収率 80.8%

溶媒

toluene

toluene

反応条件

後処理

1. 1
   その他to be degassed while the pressure
2. 2
   workup.STIRRINGThis mixture was stirred at 80° C. for 3 hours under a stream of nitrogen
3. 3
   workup.STIRRINGThe mixture was stirred for approximately 30 minutes
4. 4
   洗浄washed with water
5. 5
   乾燥After the washing, an organic layer was dried with magnesium sulfate
6. 6
   ろ過This mixture was subjected to gravity filtration
7. 7
   その他condensed
8. 8
   その他to give an oily substance
9. 9
   ろ過This solution was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855)
10. 10
    濃縮The obtained filtrate was concentrated

実験手順

2.5 g (10 mmol) of 3-bromocarbazole, 2.9 g (10 mmol) of N-phenylcarbazol-3-boronic acid, and 152 mg (0.50 mmol) of tri(ortho-tolyl)phosphine were put into a 200 mL three-neck flask, and the atmosphere in the flask was substituted by nitrogen. 50 mL of dimethoxyethanol (DME) and 10 mL (2 mol/L) of an aqueous solution of potassium carbonate were added to this mixture. This mixture was stirred to be degassed while the pressure was reduced. After the degassing, 50 mg (0.2 mmol) of palladium acetate was added to the mixture. This mixture was stirred at 80° C. for 3 hours under a stream of nitrogen. After the stirring, approximately 50 mL of toluene was added to this mixture. The mixture was stirred for approximately 30 minutes and then washed with water and a saturated saline solution in this order. After the washing, an organic layer was dried with magnesium sulfate. This mixture was subjected to gravity filtration. The obtained filtrate was condensed to give an oily substance. The obtained oily substance was dissolved in toluene. This solution was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The obtained filtrate was concentrated to give 3.3 g of a white solid, which was the object of the synthesis, at a yield of 80%.

出典