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[ CAS No. 918137-84-5 ] {[proInfo.proName]}

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Chemical Structure| 918137-84-5
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CAS No. :918137-84-5 MDL No. :MFCD32184599
Formula : C36H23BrN2 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 563.49 Pubchem ID :-
Synonyms :

Safety of [ 918137-84-5 ]

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Application In Synthesis of [ 918137-84-5 ]

* 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 [ 918137-84-5 ]

[ 918137-84-5 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 854952-58-2 ]
  • [ 57103-20-5 ]
  • [ 918137-84-5 ]
YieldReaction ConditionsOperation in experiment
38% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water;Inert atmosphere; Heating; In a three-necked flask equipped with a stirrer 2.50 g (6.23 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenylcarbazole</strong> (compound a), 1.79 g (6.23 mmol) of 9-phenylcarbazole-3-boronic acid (compound b), 41.6 ml of 2 M potassium carbonate (K2CO3) aqueous solution (83.2 mmol of potassium carbonate) and 125 ml of tetrahydrofuran (THF) were added and nitrogen bubbling was carried out for 1 hour. 350 mg (0.31 mmol) of tetrakis (triphenylphosphine)palladium (Pd (PPh 3) 4) was added thereto and heated and stirred overnight. The reaction solution was returned to room temperature and the solvent was distilled off. After adding dichloromethane to the residue and redissolving it, and then washed with a saturated saline solution. Anhydrous magnesium sulfate was added to the organic layer, and the organic layer was dried and filtered. After concentrating the filtrate, silica gel column chromatography (dichloromethane: hexane = 1: 4) was carried out, a target compound c was obtained in a yield of 1.32 g (0.24 mmol) in a yield of 38percent.
32% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 16h;Inert atmosphere; 100 g (348 mmol) of 9-phenyl-9H-carbazol-3-ylboronic acid was dissolved in 1.3 L of tetrahydrofuran (THF) in a nitrogen environment, 168 g (418 mmol) of <strong>[57103-20-5]3,6-dibromo-9-phenyl-9H-carbazole</strong> and 4.02 g, 3.48 mmol) of tetrakis(triphenylphosphine)palladium were added thereto, and the mixture was agitated. 102 g (696 mmol) of potassium carbonate saturated in water was added thereto, and the mixture was heated and refluxed at 80 °C for 16 hours. When the reaction was terminated, water was added to the reaction solution, and the mixture was extracted with dichloromethane (DCM) and treated with anhydrous MgSO4 to remove moisture and then, filtered and concentrated under a reduced pressure. The obtained residue was separated and purified through flash column chromatography, obtaining a compound I-28 (62.8 g, 32 percent). HRMS (70 eV, EI+): m/z calcd for C36H23BrN2: 562.1045, found: 562.1. Elemental Analysis: C, 77 percent; H, 4 percent
Reference： [1]Journal of Materials Chemistry C,2013,vol. 1,p. 8177 - 8185
[2]Synlett,2006,p. 2841 - 2845
[3]Patent: JP2017/145198,2017,A .Location in patent: Paragraph 0043-0044
[4]Patent: EP2889296,2015,A1 .Location in patent: Paragraph 0265-0268
  • 2
  • [ 918137-84-5 ]
  • [ 108847-20-7 ]
  • [ 1799958-69-2 ]
YieldReaction ConditionsOperation in experiment
83% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 60℃; for 8h; Inert atmosphere; 4.4. Synthesis of materials 6-bromo-9,9’-diphenyl-3,3’-bicarbazole (2.63 g,4.66 mmol), dibenzo[b,d]thiophen-4-yl boronic acid (1.15 g,5.04 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.26 g,0.23 mmol) were dissolved in THF/2 M K2CO3 (3/1, v/v). The reactionmixture was heated to 60 C for 8 h under an argon atmosphere.After cooling to room temperature, the organic layer wasseparated and evaporated to remove solvent. The residue was purifiedby column chromatography with 1:3 (v/v) dichloromethane/petroleum ether as the eluent and recrystallized fromdichloromethane/petroleum to give a white crystalline powder(2.58 g, 83%).
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene Reflux; 6 Preparation of compound ref 6 Dibenzo [b, d] thiophen-4-ylboronic acid, 4.3 g, 19.0 mM), 6-bromo-9,9'-diphenyl-9H, 9'H-3,3'-bicarbazole, 10.7g, 19.0mM), Pd (PPh3 )41.1 g (0.95 mM) of K2CO3 and 5.2 g (38.0 mM) of K2CO3 were dissolved in toluene / EtOH / H2O 100/20/20 mL and refluxed for 12 hours. Reaction CompleteAfter distilled water and DCM were added at room temperature, the organic layer was extracted with MgSO 4 and the solvent was removed using a rotary evaporatorAll. The reaction product was purified by column chromatography (DCM: Hex = 1: 3) and recrystallized from methanol to obtain desired compound ref 68.9 g (70%) was obtained.
70% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 12h; Reflux; 5 Preparation Example 5] Preparation of compound ref 6 Dibenzo [b, d] thiophen-4-ylboronic acid (dibenzo [b, d] thiophen-4-ylboronic acid, 4.3 g, 19.0 mM), 6-bromo-9,9'-diphenyl-9H, 9'H-3,3'-bicarbazole (6-bromo-9,9'-diphenyl-9H,9'H-3,3'-bicarbazole, 10.7 g, 19.0 mM), Pd(PPh3)4 1.1 g (0.95 mM), 5.2 g (38.0 mM) of K2CO3 was dissolved in toluene/EtOH/H2O 100/20/20 mL and refluxed for 12 hours. After the reaction was completed, distilled water and DCM were added at room temperature for extraction, and the organic layer was dried over MgSO4 and the solvent was removed by a rotary evaporator. The reaction product was purified by column chromatography (DCM:Hex=1:3) and recrystallized from methanol to obtain 8.9 g (70%) of the target compound ref 6 .
Reference： [1]Xie, Yue-Min; Cui, Lin-Song; Zu, Feng-Shuo; Igbari, Femi; Xue, Miao-Miao; Jiang, Zuo-Quan; Liao, Liang-Sheng [Organic electronics, 2015, vol. 26, p. 25 - 29]
[2]Current Patent Assignee: LT SAMBO CO LTD - KR101693744, 2017, B1 Location in patent: Paragraph 0147-0149
[3]Current Patent Assignee: LT SAMBO CO LTD - KR102143580, 2020, B1 Location in patent: Paragraph 0348-0350
  • 3
  • [ 918137-84-5 ]
  • [ 100124-06-9 ]
  • [ 1699728-83-0 ]
YieldReaction ConditionsOperation in experiment
85% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In tetrahydrofuran at 60℃; for 8h; Inert atmosphere; 4.4. Synthesis of materials General procedure: 6-bromo-9,9’-diphenyl-3,3’-bicarbazole (2.63 g,4.66 mmol), dibenzo[b,d]thiophen-4-yl boronic acid (1.15 g,5.04 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.26 g,0.23 mmol) were dissolved in THF/2 M K2CO3 (3/1, v/v). The reactionmixture was heated to 60 C for 8 h under an argon atmosphere.After cooling to room temperature, the organic layer wasseparated and evaporated to remove solvent. The residue was purifiedby column chromatography with 1:3 (v/v) dichloromethane/petroleum ether as the eluent and recrystallized fromdichloromethane/petroleum to give a white crystalline powder(2.58 g, 83%).
Reference： [1]Xie, Yue-Min; Cui, Lin-Song; Zu, Feng-Shuo; Igbari, Femi; Xue, Miao-Miao; Jiang, Zuo-Quan; Liao, Liang-Sheng [Organic electronics, 2015, vol. 26, p. 25 - 29]
  • 4
  • [ 918137-84-5 ]
  • [ 60511-85-5 ]
  • C54H34N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
47% With copper(l) iodide; potassium carbonate; In quinoline; at 190℃; for 72h;Sealed tube; In a pressure-resistant tube equipped with a stirring bar, 500 mg (0.89 mmol) of compound c, 226 mg (0.89 mmol) of <strong>[60511-85-5]11,12-dihydroindolo[2,3-a]carbazole</strong> (compound 1), 30 mg (5.30 mmol) of potassium carbonate, 600 mg (3.17 mg) of copper iodide (CuI), quinoline 9 ml was added, after depressurization, sealed, the mixture was stirred at a bath temperature of 190 C. for 72 hours. The reaction solution was cooled to room temperature, dichloromethane was added thereto, and the solution was redissolved, and then saturated brine . Anhydrous magnesium sulfate was added to the organic layer, and the organic layer was dried and filtered. The filtrate was concentrated and then subjected to silica gel column chromatography (dichloromethane: hexane = 3: 7) , 311 mg (0.42 mmol) of compound d was obtained in a yield of 47%.
Reference： [1]Patent: JP2017/145198,2017,A .Location in patent: Paragraph 0043; 0045-0046

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