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ChemicalBook CAS DataBase List 3,6-Diphenyl-9H-carbazole
56525-79-2

3,6-Diphenyl-9H-carbazole synthesis

11synthesis methods
3,6-Dibromocarbazole

6825-20-3

Phenylboronic acid

98-80-6

3,6-Diphenyl-9H-carbazole

56525-79-2

Under nitrogen protection, 3,6-dibromocarbazole (5 g, 15.4 mmol), phenylboronic acid (4.1 g, 33.9 mmol), palladium triphenylphosphine (0.7 g, 0.6 mmol) and toluene (45 ml) were sequentially added to a dry reaction flask. Subsequently, 2M aqueous sodium carbonate solution (45 ml) was slowly added. The reaction mixture was stirred at 80°C for 8 hours. After completion of the reaction, the organic phase was separated and concentrated under reduced pressure using a rotary evaporator. Finally, the concentrated residue was purified by silica gel column chromatography to afford the target product 3,6-diphenylcarbazole (3.6 g, 74% yield).

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Yield:56525-79-2 89%

Reaction Conditions:

with tetrabutylammomium bromide;sodium carbonate;palladium dichloride in acetone; for 36 h;Reflux;Inert atmosphere;

Steps:

1.I; 5.I; 9.I (I) Synthesis of 3,6-diphenyl-9H-carbazole, the reaction formula is as follows

Add 3,6-dibromo-9H-carbazole (2.6g, 8mmol), NaBPh4 (2.736g, 8mmol), tetrabutylammonium bromide (TBAB) (0.12g, 0.5mmol), chlorinated into a 250mL three-necked flask Palladium (0.05g, 0.25mmol), 30ml of 2M sodium carbonate solution, 120ml of acetone, reflux for 36h under nitrogen.The acetone was evaporated, and the aqueous layer was extracted with dichloromethane. The extract was washed with water and dried over anhydrous magnesium sulfate. The white flocculent product 3,6-diphenyl-9H-carbazole (2.3g, yields: 89%), the eluent is petroleum ether: dichloromethane = 2:1.Melting point: 177.1°C.

References:

CN107602443,2020,B Location in patent:Paragraph 0030-0040; 0133; 0134; 0201; 0202

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