1-(4-Bromophenyl)-naphthlene

off-white powder

Under an argon gas atmosphere, 200.0 g (1.163 mol) of 1-naphthaleneboronic acid, 329.0 g (1.163 mol) of 4-bromoiodobenzene, 26.9 g (23.3 mmol) of tetrakis(triphenylphosphine)palladium(0), 3.7 L of toluene and 1.74 L of aqueous solution of 2M sodium carbonate were added together, and stirred at 90 degrees C. for 24 hours. After the reaction was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. The organic phase thereof was washed by water and dried with magnesium sulfate, and the toluene was then distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 268 g of 1-(4-bromophenyl) naphthalene was obtained at an yield of 81percent.1.72 g (10 mmol) of Intermediate-2 and 2.83 g (10 mmol) of 1-bromo-4-iodobenzene were introduced under nitrogen and dissolved in 30 ml of toluene0.58 g (0.5 mmol) of Pd (PPh3) 4 and 15 ml (30 mmol) of 2M K2CO3 were added, respectively, and refluxed for 24 hours. After the completion of the reaction, the temperature of the reaction mixture was cooled to room temperature, 150 ml of MC and 150 ml of H2O were added to extract the MC layer, Dried over MgSO4, concentrated and then columned with Hex: EA = 5: 1 to yield Intermediate-5 2.29 (81percent).3-A. Production of compound 3a; [87] After l-bromo-4-iodobenzene (10 g, 35.35 mmol) and 1-naphthalene bromic acid(5.47 g, 31.82 mmol) were dissolved in anhydrous THF (100 mL), Pd(PPhStep 1-1: To a 3 L three-neck flask were added 47 g (0.28 mol) of l -naphthaleneboronic acid and 82 g (0.29 mol) of 4-bromoiodobenzene and added 750 mL of toluene and 250 mL of ethanol. The mixture was degassed by being stirred while the pressure was being reduced, and after the degassing, the atmosphere in the flask was replaced with nitrogen. To the solution was added 415 mL of an aqueous solution of potassium carbonate (2.0 mol L). The mixture was degassed again by being stirred while the pressure was being reduced, and after the degassing, the atmosphere in the flask was replaced with nitrogen. Further, 4.2 g (14 mmol) of tri(o / ' -tolyl)phosphine and 0.7 g (2.8 mmol) of palladium(Il) acetate were added. This mixture was stirred at 90 °C for 1 hour under a nitrogen stream. After the stirring, the mixture was naturally cooled to room temperature, and the aqueous layer of the mixture was extracted three times with toluene. The resulting solution of the extract and the organic layer were combined and washed twice with water and twice with a saturated aqueous solution of sodium chloride. Then, magnesium sulfate was added, and the mixture was left still for 18 hours for drying. The mixture was subjected to gravity filtration to remove magnesium sulfate, and the resulting filtrate was concentrated to give an orange liquid. To the orange liquid was added 500 mL of hexane, and the resulting solution was purified through Celite and Florisil. The obtained filtrate was concentrated to give a colorless liquid. To the colorless liquid was added hexane, and the mixture was left still at -10 °C, and the precipitated impurities were separated by filtration. The resulting filtrate was concentrated to give a colorless liquid. The colorless liquid was purified by distillation under reduced pressure, and the resulting yellow liquid was purified by silica gel column chromatography (developing solvent: hexane) to give 56 g of a target colorless liquid in a yield of 72 percentStep 1: Synthesis of l-(4-bromophenyl)-naphthalene][0836]A synthetic scheme of l-(4-bromophenyl)-naphthalene in Step 1 is shown in the following (W-I). In a 500-mL three-neck flask, 46g (160 mmol) of 4-bromoiodobenzene, 24 g (140 mmol) of 1-naphthaleneboronic acid, 45 mg (0.2 mmol) of palladium(II) acetate, and 60 mg (0.2 mmol) of tri(o-tolyl)phosphine were put, and 100 mL of toluene, 20 mL of ethanol, and 11 mL of a potassium carbonate aqueous solution (2 mol/L) were added to this mixture. This mixture was deaerated while being stirred under low pressure. After the deaeration, the mixture was stirred under a nitrogen atmosphere at 90 Synthesis In this example, a synthesis method of 4-bromo-4'-(1-naphthyl)diphenylamine (abbreviation: BrNBA), which is represented by the following structural formula (100) is described.; Step 1: Synthesis of 1-(4-bromophenyl)-naphthalene; In a 500-mL three-neck flask, 46 g (160 mmol) of 4-bromoiodobenzene, 24 g (140 mmol) of 1-naphthaleneboronic acid, 45 mg (0.2 mmol) of palladium(II) acetate, and 60 mg (0.2 mmol) of tris(o-tolyl)phosphine were put, and 100 mL of toluene, 20 mL of ethanol, and 11 mL of a potassium carbonate solution (2 mol/L) were added thereto. This mixture was degassed while being stirred under reduced pressure. After that, the mixture was stirred under a nitrogen atmosphere at 90° C. for 4 hours to be reacted.After the reaction, 500 mL of toluene was added to the reaction mixture solution, and the resulting suspension was filtrated through Florisil (Catalog No. 540-00135, produced by Wako Pure Chemical Industries, Ltd.) and Celite (Catalog No. 531-16855, produced by Wako Pure Chemical Industries, Ltd.). The obtained filtrate was washed with water, and magnesium sulfate was added thereto to adsorb moisture. This suspension was filtrated through Florisil and Celite to obtain a filtrate. The obtained filtrate was concentrated and purified by silica gel column chromatography (developing solvent: hexane). The obtained fraction was concentrated to obtain 25 g of a colorless transparent liquid which was a desired substance in a yield of 62percent. A reaction of the above synthesis method is shown in the following scheme (F-1). An Rf value of the desired substance by a silica gel thin layer chromatography (TLC) (developing solvent: hexane) was 0.38 and that of 4-bromoiodobenzene was 0.57.The following components were loaded into a 100-ml recovery flask, and the whole was stirred in a stream of nitrogen at 4OStep 1: Synthesis of Intermediate (C)15 g (63 mmol) of 1, 4-dibromobenzene, 7.66 g (44 mmol) of 1-naphthaleneboron acid, 17.58 g (127 mmol) of potassium carbonate, and 1.83 g (50 mmol) of tetrakis-(triphenylphosphine) palladium were suspended in a mixed solvent including 200 ml of tetrahydrofuran, 200 ml of toluene, and 50 ml of purified water, and heated and refluxed under a nitrogen atmosphere for 24 hours.The reaction fluid was cooled to room temperature, and separated into two layers. Then, the solvent of an organic layer thereof was removed under a reduced pressure to provide a fluid. The fluid was separated by column chromatography (hexane) to remove the solvent and to provide 15 g of a gel intermediate (C) at a yield of 83percent.The starting material, 1, 4-dibromobenzene (30 g, 127 mmol) to THF (560 mL) after the dissolved, naphthalen-1-ylboronic acid (21.9 g, 127 mmol), Pd (PPh3) 4 (4.41 g, 3.82 mmol ), K2CO3 (52.7 g, 381 mmol), followed by the addition of water (280 mL), stirred and refluxed. When the reaction is complete, the ether was extracted with water, the organic layer was concentrated and then the next, the resulting product to the organic was dried with MgSO4 and concentrated to silicagel column and recrystallization. To obtain 23 g (Yield: 64percent)

Molecular Weight:283.16
XLogP3:5.5
Rotatable Bond Count:1
Exact Mass:282.00441
Monoisotopic Mass:282.00441
Heavy Atom Count:17
Complexity:242
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes