9-(4-phenylphenyl)carbazole

Step 1 : Synthesis of 9-(biphenyl-4-yl)-9H-carbazole] [0583]A synthetic scheme of 9-(biphenyl-4-yl)-9H-carbazole in Step 1 is shown in the Under an argon atmosphere, 167 mg (1.0 mmol) of carbazole, 233 mg (1.0 mmol) of 4-bromobiphenyl, 4.6 mg (0.005 mmol) of tris(dibenzylideneacetone)dipalladium, 125 mg (1.3 mmol) of sodium tert-butoxide, 2 mL of toluene, and 5.9 mg (0.01 mmol) of dicyclohexyl[2-(1-pyrenyl)phenyl]phosphine obtained in Example 2, was added. The reaction vessel was sealed and then stirred at 120 °C.for 12 hours. After cooling the reaction vessel to room temperature, the mixture was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 0 to 19: 1) 9-[(1, 1'-biphenyl)-4-yl]-9H-carbazole 296 mg (white solid, yield 93percent) was obtained.12 g (50 mmol) of 4-bromobiphenyl, 8.4 g (50 mmol) of carbazole, 230 mg (1 mmol) of palladium acetate, 1.8 g (3.0 mmol) of l, l-bis(diphenylphosphino)ferrocene, and 13 g (180 mmol) of sodium-terf-butoxide were added in a three-neck flask and the atmosphere of the flask was substituted by nitrogen, and then, 80 mL of dehydrogenated xylene was added, and deaerated. Under nitrogen atmosphere, it was stirred at 120 0.3120 mol of 4-iodobiphenyl, 0.2400 mol of carbazole, 0.0184 mol of phenanthroline, cuprous iodide0.0184 mol, cesium carbonate 0.4080 mol was charged into a 1000 ml three-necked flask, dissolved in 300 ml of DMF, and evacuated to nitrogenThree times, the temperature to 153 ° C, the reaction overnight. The reaction solution was passed through a silica gel funnel and rinsed with methylene chloride until no product was releasedAbout 400ml with 500ml of water, liquid, take dichloromethane phase, washed with water three times; spin dry, add 100ml dissolved, add500ml of ethanol has a large amount of solid precipitation, suction filtration, vacuum drying at 55 . To give 9- (4-biphenyl) -9H-carbazole 0.2130 mol, Yield 88.75percentUnder an argon atmosphere, 167 mg (1.0 mmol) of carbazole, 233 mg (1.0 mmol) of 4-bromobiphenyl, 4.6 mg (0.005 mmol) of tris(dibenzylideneacetone)dipalladium, 125 mg (1.3 mmol) of sodium tert-butoxide, 2 mL of toluene, and 5.9 mg (0.01 mmol) of dicyclohexyl[2-(1-pyrenyl)phenyl]phosphine obtained in Example 2, was added. The reaction vessel was sealed and then stirred at 120 °C.for 12 hours. After cooling the reaction vessel to room temperature, the mixture was purified by silica gel column chromatography (hexane: ethyl acetate = 20: 0 to 19: 1) 9-[(1, 1'-biphenyl)-4-yl]-9H-carbazole 296 mg (white solid, yield 93percent) was obtained.12 g (50 mmol) of 4-bromobiphenyl, 8.4 g (50 mmol) of carbazole, 230 mg (1 mmol) of palladium acetate, 1.8 g (3.0 mmol) of l, l-bis(diphenylphosphino)ferrocene, and 13 g (180 mmol) of sodium-terf-butoxide were added in a three-neck flask and the atmosphere of the flask was substituted by nitrogen, and then, 80 mL of dehydrogenated xylene was added, and deaerated. Under nitrogen atmosphere, it was stirred at 120 0C for 7.5 hours. After the termination of the reaction, about 600 mL of heated toluene was added to this suspension, and filtrated twice through florisil, alumina and Celite.(R).. The obtained filtrate was concentrated and hexane was added thereto, recrystallization was conducted. This was filtrated, and the residue was collected and dried to obtain 14 g (the yield: 87percent) of 9-(4-biphenylyl) carbazole which was cream-colored powder. [0234] [Step 2] A synthesis method of 3-bromo-9-(4-biphenylyl)carbazole is described. A synthesis scheme of 3-bromo-9-(4-biphenylyl)carbazole is shown by (B-2).Under an atmospheric argon gas flow, blending 3.3 g of carbazole, 5.1 g of 4-bromo biphenyl, 231 mg of Pd2(dba)3, 325 mg of P(t-Bu)3, 2.9 g of t-butoxysodium and toluene, the reaction was allowed to proceed at 80 °C for 4 h. The resultant solution was cooled down and after adding toluene; it was filtered through sellite and was condensed. Purifying the resultant mixture by means of a silicagel chromatography (hexane : dichloromethane =6 : 1), the resultant solid was washed with n-hexane, vacuum dried to obtain 4.1 g of white solid, which was analyzed by FD-MS and identified as Intermediate 17.(3.48 g, 20.8 mmol), 4-bromobiphenyl (4.62 g, 19.8 mmol), sodium tert-butoxide (3.82 g, 39.8 mmol), tri-tert-butylphosphine (200 mg, 0.99 mmol) and palladium acetate (II) (101 mg, 0.45 mmol) was refluxed in dehydrated toluene (30 mL) under a nitrogen atmosphere for 48 h. After cooling the solution, the toluene was removed under reduced pressure and extracted with chloroform. The crude product was washed with ether, acetone and chloroform.

Molecular Weight:319.4
XLogP3:6.6
Rotatable Bond Count:2
Exact Mass:319.136099547
Monoisotopic Mass:319.136099547
Topological Polar Surface Area:4.9
Heavy Atom Count:25
Complexity:409
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes