Reaktion #70062

Reaktionsgleichung

p-dibromobenzene

9H-carbazole

potassium carbonate

18-crown-6-ether

→

9-(4-bromophenyl)-9H-carbazole

Ausbeute 35.0%

Lösungsmittel

toluene

N,N′-dimethylpropyleneurea

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter the stirring, the mixture was cooled to 100° C
2. 2
   Temperaturthe mixture was cooled to room temperature
3. 3
   FiltrationAfter the cooling, this mixture was subjected to suction filtration so that the precipitate
4. 4
   Sonstigewas removed
5. 5
   WaschenThe obtained filtrate was washed with dilute hydrochloric acid
6. 6
   TrocknenThe organic layer was dried with magnesium sulfate
7. 7
   FiltrationThen, the mixture was subjected to gravity filtration
8. 8
   Sonstigecondensed
9. 9
   Sonstigeto give an oily substance
10. 10
    SonstigeThis oily substance was purified by silica gel column chromatography (a developing solvent
11. 11
    Sonstigeether acetate=9:1), and then recrystallized with chloroform/hexane
12. 12
    Sonstigeto give 21 g of a light brown plate-like crystal, which
13. 13
    Sonstigethe object of the synthesis
14. 14
    SonstigeA synthesis scheme of Step 1

Vorschrift

56 g (240 mmol) of p-dibromobenzene, 31 g (180 mmol) of 9H-carbazole, 4.6 g (24 mmol) of copper(I) iodide, 66 g (480 mmol) of potassium carbonate, and 2.1 g (8 mmol) of 18-crown-6-ether were put into a 300 mL three-neck flask. The mixture was heated at about 100° C., and then 8 mL of N,N′-dimethylpropyleneurea (DMPU) was added thereto. This mixture was stirred at 180° C. for 6 hours. After the stirring, the mixture was cooled to 100° C. To the mixture was added about 200 mL of toluene, and then the mixture was cooled to room temperature. After the cooling, this mixture was subjected to suction filtration so that the precipitate was removed. The obtained filtrate was washed with dilute hydrochloric acid, a saturated sodium hydrogen carbonate solution, and a saturated saline solution in this order. The organic layer was dried with magnesium sulfate. Then, the mixture was subjected to gravity filtration. The obtained filtrate was condensed to give an oily substance. This oily substance was purified by silica gel column chromatography (a developing solvent was a mixed solvent of hexane:ether acetate=9:1), and then recrystallized with chloroform/hexane to give 21 g of a light brown plate-like crystal, which was the object of the synthesis, at a yield of 35%. A synthesis scheme of Step 1 is shown in (f-1) given below.

Quelle