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[ CAS No. 102113-98-4 ] Bis-biphenyl-4-yl-amine 15/11/2022
[ CAS No. 102113-98-4 ] Bis-biphenyl-4-yl-amine Spectrum Chemical manufactures and distributes fine chemicals with quality you can count on including those with CAS number 102113-98-4, You can be assured that all Bis(4-biphenylyl)amine products offered by Spectrum, meet or exceed the grade requirements or specifications for each individual product.Get more news about 102113-98-4,you can vist our website!
Compound I-2 (23.7 g, 73.8 mmol) was sequentially added to a round bottom flask.Compound II-2 (20.9 g, 73.8 mmol),t-BuONa (10.7 g, 111 mmol),Pd(OAc)2 (0.33 g, 1.47 mmol) and ultrasonically deoxygenated toluene (1.5 L),Reflux overnight under nitrogen,After the reaction solution was cooled, treated with ethyl acetate and water,The resulting organic layer was dried over MgSO4.The solvent was distilled off under reduced pressure to give a crude product of compound III-2.Silica gel as stationary phase, dichloromethane/hexane as eluent,The crude product was subjected to column chromatography to give Compound III-2 (28.8 g, 82percent)
Compound I-3 (23.7 g, 73.8 mmol) was sequentially added to a round bottom flask.Compound II-3 (20.9 g, 73.8 mmol),t-BuONa (10.7 g, 111 mmol),Pd(OAc)2 (0.33 g, 1.47 mmol) and ultrasonically deoxygenated toluene (1.5 L),Reflux overnight under nitrogen,After the reaction solution was cooled, treated with ethyl acetate and water,The resulting organic layer was dried over MgSO4.Evaporate the solvent under reduced pressureThe crude compound III-3 was obtained,With silicone as the stationary phase,Dichloromethane/hexane as eluent,The crude product is subjected to column chromatography.Compound III-3 (28.8 g, 82percent) was obtained.
Compound I-2 (23.7 g, 73.8 mmol), compound II-2 (20.9 g, 73.8 mmol) were sequentially added to a round bottom flask.t-BuONa (10.7 g, 111 mmol), Pd(OAc) 2 (0.33 g, 1.47 mmol), and ultrasonically deoxygenated toluene (1.5 L),After refluxing under nitrogen, the reaction solution was cooled and treated with ethyl acetate and water.The resulting organic layer was dried over MgSO 4 and the solvent was evaporated under reduced pressure.Obtained crude product of compound III-2 with silica gel as the stationary phase,Column chromatography of the crude product with dichloromethane/hexane as eluent afforded compound III-2 (28.8 g, 82percent).
Compound B-6 (39.04 g, 138 mmol) was added to the reaction vessel in that order.Compound F-6 (40.34g,125.5 mmol), Pd2 (dba) 3 (5.74 g, 6.3 mmol),P(t-Bu)3 (2.54g, 12.5mmol),After NaOt-Bu (36.2 g, 376.4 mmol) and toluene 1500 mL, the reaction was carried out at 100 ° C.After the reaction, the organic matter is extracted with diethyl ether and water.The organic layer was dried over magnesium sulfate and then concentrated to afford compound C-6 (47.83 g, 80percent).
Synthesis of Intermediate 3; 8.5 g (30 mmol) of 4-bromoiodobenzene, 6.45 g (20 mmol) of Intermediate 2, 4.3 g (45 mmol) of t-BuONa, 0.55 g (0.6 mmol) of Pd2(dba)3, and 0.12 g (0.6 mmol) of P(t-Bu)3 were dissolved in 100 mL of toluene and stirred at 90°C for 3 hours. After the reaction was completed, the reaction product was cooled to room temperature and extracted three times with distilled water and 100 ml of diethylether. An organic layer was collected and dried using magnesium sulfate to evaporate the solvent. The residue was separated and purified using silica gel column chromatography to obtain 7.53 g (yield: 79percent) of Intermediate 3.
Add 32.1 g (100 mmol, 1.0 eq.) to a dry 1 L three-necked flask.Bis(4-biphenyl)amine and 56.4 g (200 mmol, 2.0 eq.) of p-bromoiodobenzene,Add 500 ml of toluene and stir to dissolve, and add 11.5 g (120 mmol, 1.2 eq) of sodium tert-butoxide.With nitrogen for 15 minutes, 0.9 g (1 mmol, 0.01 eq) of tris(dibenzylideneacetone)dipalladium was added.Add 4 ml (2 mmol, 0.02 eq) of a solution of tri-tert-butylphosphine in toluene (10percent),Nitrogen protection, heating to 60 ° C, reaction for 3 hours, the reaction is completed.Cool to room temperature, suction filtration, wash the filter cake with water, wash the filter cake with ethanol, and beat it with ethanol 3 times.The filter cake was recrystallized from toluene to give 37.0 g of Intermediate-5, yield 78percent. 4-bromo-iodobenzene (3.4g, 12 mmol), bis-diphenyl-amine (3.86g, 12 mmol) was dissolved in N, N- dimethylacetamide and 50ml, copper chloride (CuCl) (164 mg, 1.2 mmol), followed by the addition of 2,2'- bipyridyl (187 mg, 1.2 mmol), and reflux was conducted in a nitrogen atmosphere for 12 hours. After cooling to room temperature, distilled water (200mL) added to the reaction solution to complete the reaction, it is extracted with with chloroform (3 x 100 mL). The organic layer was dried over magnesium sulfate, and distilled under reduced pressure. The product was recrystallized from ethyl ether and hexane to prepare the Formula B-1 (3.7g, 65percent).
After introducing 10 g of compound B (31 mmol), 13.2 g of 1-bromo-4-iodobenzene (46 mmol), 855 mg of tris(dibenzylideneacetone)dipalladium(0) (0.9 mmol), 757 mg of tri(o-tolyl)phosphine (2.5 mmol), 6 g of sodium tert-butoxide (62 mmol), and 310 mL of toluene into a reaction vessel, the mixture was stirred for 4 hours at 120. After completion of the reaction, the reaction product was cooled to room temperature, and then was extracted with ethyl acetate. After drying the extracted organic layer with magnesium sulfate, the solvent was removed with a rotary evaporator. Thereafter, the resulting product was purified by column chromatography to obtain 7 g of compound 2-1 (47 percent).
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