3-Iodo-N-phenylcarbazole

White crystalline powder

2.433 g (10 mmol) of the intermediate compound A was added to 100 mL of 80percent acetic acid, and then 1.357 g (5.35 mmol) of iodine (ISynthesis of Intermediate F; Intermediate E (2.433 g, 10 mmol) was added to an 80percent acetic acid (100 ml), and iodine (I2.433 g of phenylcarbazole (10 mmol) was added into 100 ml of 80percent acetic acid, and 1.357 g of Iodine (I78.9 g (0.324 mol) of the compound represented by the formula 1-a obtained in the above reaction formula 1, 44.4 g (0.175 mol) of iodine, 11.1 g (0.0486 mol) of periodic acid, Acetic acid (500 mL) was added thereto, followed by stirring at 80 ° C for 2 hours.The reaction was cooled to room temperature and extracted with diethyl ether and water. The organic layer was dehydrated with magnesium sulfate, concentrated under reduced pressure, and subjected to column chromatography using hexane as a developing solvent to obtain 88.0 g (85percent) of the compound represented by the formula (1-b).Into a mixture of 17.7 g (72.7 mmol) of 9-phenylcarbazole, 6.03 g (36.3 mmol) of potassium iodide and 7.78 g (36.4 mmol) of potassium iodate, 5.9 ml of sulfuric acid and 70 ml of ethanol were added, and the resultant mixture was stirred at 75 °C for 2 h. After cooling, the reaction production was added with water and ethyl acetate and liquid-liquid extracted. The organic layer was washed with an aqueous solution of sodium hydrogencarbonate and water and then concentrated. The obtained crude product was purified by silica gel column chromatography, to obtain 21.8 g of a white solid, which was identified as the following intermediate 1-7 by FD-MS analysis (yield: 81percent).400 mL of 85percent acetic acid was added to a mixture including 24.3 g (100.0 mmol) of phenyl carbazole, 13.4 g (50.3 mmol) of iodine, and 2.2 g (10.0 mmol) of periodic acid, and the mixture was heated at 80° C. for 4 hours. 500 mL of cold water was added to the reaction mixture, and the reaction mixture was stirred and filtered. A solid phase obtained by the filtration was cleaned with cold water several times. Then, the solid phase was dissolved in 400 mL of ethyl ether, dried, filtered, concentrated, and then separated using column chromatography to obtain 28.7 g of compound 4 in white solid form with a yield of 78percent. The structure of compound 4 was identified using HR-MS. (calc.: 369.0014, found: 369.0001)500 g of methanol and 65.19 g (0.2568 mol) of iodine were added to 125 g (0.5137 mol) of Intermediate G, and the mixture was cooled to 5 or lower. 10 g (0.1 mol) of sulfuric acid was added to 500 g of water and diluted. While the cooled reactor was maintained at 5 ° C or lower, the diluted sulfuric acid aqueous solution was slowly added dropwise and stirred for 20 hours while maintaining the same temperature condition. The reaction mixture was concentrated under reduced pressure to remove methanol, 450 g of toluene was added thereto, and the organic layer was separated. The toluene was removed by concentration under reduced pressure, and 400 g of methanol was added thereto, followed by refluxing, cooling, filtration and drying to obtain 146 g (yield: 77percent) of intermediate H having a purity of 98.3percent .To 125 g (0.5137 mol) of Intermediate G, 500 g of methanol, 65.19 g (0.2568 mol) of iodine was added and cooled to 5°C or lower.10 g (0.1 mol) of sulfuric acid was added to 500 g of water, diluted, and the cooled reactor was slowly added dropwise while keeping the temperature at 5°C or lower. After completing the drop, The reaction was completed by stirring for 20 hours while maintaining the same temperature conditions.The methanol was removed by concentration under reduced pressure, 450 g of toluene was added, the organic layer was separated, toluene was removed under reduced pressure, Methanol (400 g) was added, Cooling, filtration and drying were conducted to obtain 146 g (yield: 77percent) of Intermediate H having a purity of 98.3percent.24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodosuccinimide was slowly added thereto, and then stirring was carried out at a room temperature fro overnight. The generated precipitation was filtered and the residue was washed by a saturated sodium hydrogencarbonate water solution, water, and methanol, then was dried. 24.7g (yield 67percent) of 3-iodo-9-phenylcarbazole which was white powder, was obtained.1Og (lO.Ommol) of 9-phenyl carbazole, 838mg (5.0mmol) of potassium iodide, l.lg (5.0mmol) of potassium iodate, and 3OmL of glacial acetic acid were put in a three-neck flask and refluxed for 1 hour at 120 4.9 g (20 mmol) of N-phenylcarbazole was dissolved in 100 ml of glacial acetic acid, 4.48 g (20 mmol) of N-iodinesuccinimide was gradually added thereto, and then stirring was carried out at a room temperature overnight. The solution became clouded at 2.5 hours from the reaction started, and was suspended by a light orange precipitate at 3.5 hours from the reaction started. This suspension was dropped to 300 ml of the saturated aqueous solution of sodium chloride to obtain a light salmon pink block object. After washing this block object three times with water, 200 ml of ethyl acetate was added to dissolve the block object, and washing was carried out with sodium hydrogen carbonate and then with water. After magnesium sulfate was added to remove moisture, magnesium sulfate was removed by filtration. Recrystallization was carried out to obtain 5 g of white powder in a yield of 68 percent by heating this solution to which hexane was added.Alternatively, 3-iodine-9-phenylcarbazole also can be synthesized by the following method. 24.3 g (100 mmol) of N-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodinesuccinimide was gradually added thereto, and stirring was carried out at a room temperature overnight. The solution EPO 24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 ml of glacial acetic acid, 22.5 g (100 mmol) of N-iodosuccinimide was slowly added thereto, and then stirring was carried out at a room temperature fro overnight. The generated precipitation was filtered and the residue was washed by a saturated sodium hydrogencarbonate water solution, water, and methanol, then was dried. 24.7g (yield 67percent) of 3-iodo-9-phenylcarbazole which was white powder, was obtained.1Og (lO.Ommol) of 9-phenyl carbazole, 838mg (5.0mmol) of potassium iodide, l.lg (5.0mmol) of potassium iodate, and 3OmL of glacial acetic acid were put in a three-neck flask and refluxed for 1 hour at 120 17.7 g of 9-phenylcarbazole, 6.03 g of potassium iodide, 7.78 g of potassium iodate, 5.90 mL of sulfuric acid and ethanol were placed and reacted at 75° C. for 2 hours.After cooling, water and ethyl acetate were added thereto to be separated into a water phase and an organic phase. The organic phase was extracted, washed with sodium bicarbonate water and water, and concentrated to obtain a crude product. The crude product was purified with silica gel chromatography (with toluene), and the resultant solids were dried under reduced pressure to obtain 21.8 g of white solids. The solids were identified as Intermediate 1 by FD-MS analysis.After adding 5.90 mL of sulfuric acid and 70 mL of ethanol to 17.7 g of 9-phenylcarbazole, 6.03 g of potassiumiodide and 7.78 g of potassium iodate, the resultant mixture was allowed to react at 75 °C for 2 h. After cooling, waterand ethyl acetate were added and the resultant mixture was subjected to liquid-liquid extraction. The organic layer waswashed with an aqueous sodium hydrogen carbonate solution and water and then concentrated. The obtained crudeproduct was purified by silica gel column chromatography. The purified solid was vacuum-dried to obtain 21.8 g of whilesolid, which was identified as Intermediate 2 shown below by FD-MS analysis.

An important intermediate for the synthesis of optoelectronic materials

Molecular Weight:369.2
XLogP3:5.6
Rotatable Bond Count:1
Exact Mass:369.00145
Monoisotopic Mass:369.00145
Topological Polar Surface Area:4.9
Heavy Atom Count:20
Complexity:338
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes