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Chemical Structure| 861317-95-5 Chemical Structure| 861317-95-5

Structure of 861317-95-5

Chemical Structure| 861317-95-5

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Product Details of [ 861317-95-5 ]

CAS No. :861317-95-5
Formula : C18H13NO
M.W : 259.30
SMILES Code : C12=CC=C(NC3=CC=CC=C3)C=C1C4=CC=CC=C4O2
MDL No. :MFCD22415870
InChI Key :IABICDIEOYDAFF-UHFFFAOYSA-N
Pubchem ID :67204676

Safety of [ 861317-95-5 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 861317-95-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 861317-95-5 ]

[ 861317-95-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 5408-56-0 ]
  • [ 62-53-3 ]
  • [ 861317-95-5 ]
YieldReaction ConditionsOperation in experiment
39% With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 120℃; for 5h;Inert atmosphere; [Step 2: Method of Synthesizing N-(Dibenzofuran-2-yl)-phenylamine (Abbreviation: FrA)]In a 100-mL three-neck flask were put 4.5 g (15 mmol) of <strong>[5408-56-0]2-iododibenzofuran</strong>, 2.0 g (20 mmol) of aniline, 45 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0), and 3.0 g (30 mmol) of sodium-tert-butoxide (abbreviation: tert-BuONa), and 30 mL of dehydrated xylene was added. Then, deaeration was performed for 3 minutes until no bubbles came out. To this suspension, 0.5 mL (0.3 mmol) of tri-tert-butylphosphine (10 wt % hexane solution) was added, and then the mixture was heated and stirred at 120 C. for 5 hours in a nitrogen atmosphere to cause a reaction.About 200 mL of toluene was added to this reaction suspension, and the mixture was filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The resulting filtrate was washed with water, and magnesium sulfate was added thereto to adsorb moisture.This suspension was further filtered through Florisil, alumina, and Celite, and the resulting filtrate was concentrated. Then, methanol was added thereto, followed by irradiation with ultrasonic waves. The generated solid was collected by filtration and dried, so that the objective substance was obtained as 1.6 g of white powder in 39% yield. A reaction scheme of this synthesis method is shown in (B-2) below. The Rf values of the objective substance, <strong>[5408-56-0]2-iododibenzofuran</strong>, and aniline were respectively 0.28, 0.59, and 0.07, which were found by silica gel thin layer chromatography (TLC) (with a developing solvent of ethyl acetate and hexane in a ratio of 1:10).The compound obtained in Step 2 was subjected to a nuclear magnetic resonance (NMR) measurement. The measurement data are shown below.1NMR (CDCl3, 300 MHz):delta (ppm)=5.80 (s, 1H), 6.94-7.68 (m, 10H), 8.99 (d, J=7.8 Hz, 1H), 8.11 (s, 1H).The measurement results confirmed that the objective substance, N-(dibenzofuran-2-yl)-phenylamine (abbreviation: FrA), was obtained.
39% With sodium t-butanolate;tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); In hexane; xylene; at 120℃; for 5h;Inert atmosphere; Step 2: Method of Synthesizing N-(Dibenzofuran-2-yl)-phenylamine (Abbreviation: FrA) Into a 100 mL three-neck flask were placed 4.5 g (15 mmol) of <strong>[5408-56-0]2-iododibenzofuran</strong>, 2.0 g (20 mmol) of aniline, 45 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0), and 3.0 g (30 mmol) of sodium-tert-butoxide (abbreviation: tert-BuONa), and 30 mL of dehydrated xylene was added. Then, deaeration was performed for 3 minutes until a bubble ceased to appear. To this suspension, 0.5 mL (0.3 mmol) of tri-tert-butylphosphine (a 10 wt % hexane solution) was added, and the mixture was heated and stirred at 120 C. for 5 hours in a nitrogen atmosphere to cause a reaction. About 200 mL of toluene was added to this reaction suspension, and the mixture was filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), alumina, and Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855). The obtained filtrate was washed with water, and magnesium sulfate was added thereto to adsorb moisture. This suspension was further filtered through Florisil, alumina, and Celite, and the obtained filtrate was concentrated. Then, methanol was added thereto, and the mixture was irradiated with ultrasonic waves. The generated solid was collected by filtration and dried to give 1.6 g of a white powder in 39% yield, which was the object of the synthesis. A reaction scheme of the above synthesis method is illustrated in (B-2) below. The Rf values of the object of the synthesis, <strong>[5408-56-0]2-iododibenzofuran</strong>, and aniline were respectively 0.28, 0.59, and 0.07, which were found by silica gel thin layer chromatography (TLC) (ethyl acetate:hexane (1:10) as the developing solvent). The compound obtained in Step 2 above was subjected to nuclear magnetic resonance (NMR) spectroscopy. The measurement data are shown below. 1H NMR (CDCl3, 300 MHz): delta (ppm)-=5.80 (s, 1H), 6.94-7.68 (m, 10H), 8.99 (d, J=7.8 Hz, 1H), 8.11 (s, 1H).
  • 2
  • [ 67665-47-8 ]
  • [ 861317-95-5 ]
  • C61H38N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
86.2% With tri-tert-butyl phosphine; potassium tert-butylate; palladium diacetate; In toluene; at 100℃; for 20h;Inert atmosphere; Schlenk technique; 100 mL with argon substitution, equipped with a stirrerTo a Schlenk tube of N-phenyldibenzo [b, d] furan-4-amine (1.15 g, 4.43 mmol), <strong>[67665-47-8]2,2'-dibromo-9,9'-spirobifluorene</strong> (1.00 g, 11 mmol), palladium acetate (40 mg, 0.18 mmol), toluene (40 mL)Tri-t-butylphosphine (36 mg, 0.18 mmol) and potassium t-butoxide (1.0 g, 8.9 mmol) were placed and sealed, followed by stirring at 100 ° C. for 20 hours.Thereafter, the reaction vessel was allowed to cool to near room temperature, the lid was opened, and water (30 mL) was added thereto. The content was transferred to a separating funnel, the organic layer and the aqueous layer were separated, the aqueous layer was removed, and the organic layer was washed with water.The organic layer was dried over sodium sulfate. Thereafter, sodium sulfate was removed by filtration, and the organic layer was concentrated.The concentrated mixture was purified by silica gel column chromatography (developing solvent: hexane / dichloromethane = 3/1) to obtain the objective compound represented by the above chemical formula (31) (yield 1.51 g, yield Rate 86.2percent).
  • 3
  • [ 861317-95-5 ]
  • [ 171408-84-7 ]
  • C61H38N2O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77.9% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; potassium tert-butylate; In toluene; at 100℃; for 2h;Inert atmosphere; Schlenk technique; N-phenyldibenzo [b, d] thiophene-4-amine (1.40 g, 0.25 mmol) was added to a 100 mL Schlenk tube equipped with a stirrer and purged with argon,2,7-dibromo-9,9'-spirobifluorene (1.10 g, 2.57 mml), Pd 2 (dba) 3 (47 mg, 0.05 mmol), toluene (25 mL), tri-t -butylphosphine (10 mg, 0.05 mmol) and potassium t-butoxide (0.72 g, 6.4 mmol) were placed and sealed, followed by stirring at 100 ° C. for 2 hours.Thereafter, the reaction vessel was allowed to cool to near room temperature, the lid was opened, and water (30 mL) was added thereto. The content was transferred to a separating funnel, the organic layer and the aqueous layer were separated, the aqueous layer was removed, and the organic layer was washed with water. The organic layer was dried over sodium sulfate.Thereafter, sodium sulfate was removed by filtration, and the organic layer was concentrated. The resulting mixture was concentrated and purified by silica gel column chromatography (developing solvent: hexane / dichloromethane = 3/1) to obtain the objective compound represented by the above chemical formula (33) (yield 1.66 g, yield 77.9percent).
 

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