[ CAS No. 185626-73-7 ] {[proInfo.proName]}

Name: 185626-73-7|(3-Bromophenyl)triphenylsilane|97%
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Quality Control of [ 185626-73-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 185626-73-7 ]

CAS No. :	185626-73-7	MDL No. :	MFCD28098175
Formula :	C₂₄H₁₉BrSi	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WTYKIOBQNRWDQP-UHFFFAOYSA-N
M.W :	415.40	Pubchem ID :	85709247
Synonyms :

Safety of [ 185626-73-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 185626-73-7 ]

* 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.

Upstream synthesis route of [ 185626-73-7 ]
Downstream synthetic route of [ 185626-73-7 ]

[ 185626-73-7 ] Synthesis Path-Upstream 1~1

1
[ 76-86-8 ]
[ 108-36-1 ]
[ 185626-73-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Stage #2: at 20℃; for 12 h;	1,3-Dibromobenzene 20 g (84.77 mmol) was dissolved in THF 500 mL, and then cooled to a temperature of -78. n-BuLi 2.5M 33.9 mL(84.77 mmol) was slowly added thereinto, and then stirred at a temperature of -78 for 1 hour. Chlorotriphenylsilane ((C₆H₅)₃SiCl) 29.9 g was dissolved in THF 100 mL, and this solution was added into the above reaction mixture. The resultant mixture was slowly warmed to room temperature, and stirred for 12 hours. Then, extraction with EA, wash with distilled water and aqueous NaCl solution, drying over MgSO₄, distillation under reduced pressure, and recrystallization with MC-MeOH in the ratio of 1:10, were sequentially performed, thereby obtaining Compound 8-1 18 g(95 percent).
87%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1 h; Stage #2: at 20℃; for 24 h;	Preparation of Compound 2-3 After 1,3-dibromobenzene (11.2 g, 47 mmol) was dissolved in THF (200 mL), the mixture was cooled to -78 °C. After slowly adding n-BuLi (19 mL, 2.5M in hexane, 70.5 mmol), the mixture was stirred for 1 hour. Solution that TPS-Cl (20 g, 56.8 mmol) was dissolved in THF (25 mL) was slowly added. After slowly increasing temperature, the mixture was stirred at room temperature for one day. Upon completion of the reaction, H₂O was added and the mixture was extracted with EA/H₂O. After removing moisture with MgSO₄ and performing distillation under reduced pressure, Compound 2-3 (17 g, 87percent) was obtained by column(MC/Hexane) separation.
63%	Stage #1: at -78℃; for 0.166667 h; Inert atmosphere Stage #2: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Stage #3: at 20℃; for 12 h;	1,3-dibromobenzene (20g, 84. 77mmol) was added to the reaction vessel, and nitrogen atmosphere was created in a vacuum state. After addition of tetrahydrofuran (500mL), the mixture was stirred at -78 ° C for 10 min. After slowly added N-BuLi (2. 5M) (33. 9mL, 84. 77mmol), the mixture was stirred at -78 ° C for 1 hour. Chloro triphenylsilyl(29. 9g, 107. 72mmol) was dissolved THF (lOOmL) in, and slowly added the mixture. After stirring for 12 hours at room temperature, the reaction was complete and the mixture was washed with distilled water. Extracted with EA, and the organic layer was dried with MgS04, using a rotary evaporatorAnd slowly added to the solvent. To give compound A-4 (62g, 63percent) was recrystallized from MC and Μ0Η

63%

Stage #1: at -78℃; for 0.166667 h; Inert atmosphere
Stage #2: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Inert atmosphere
Stage #3: at 20℃; for 12 h; Inert atmosphere

20g (84.77mmol) 1,3-dibromobenzene in a reaction vessel to create a vacuum with nitrogen atmosphere was added 500mL THF was stirred at -78 °C 10 minutes. 33.9 mL (84.77 mmol) of n-BuLi (2.5 M) was slowly added thereto, followed by stirring at -78 °C for 1 hour. 29.9 g (107.72 mmol) of chlorotriphenylsilane was dissolved in 100 mL of THF and then slowly added. After stirring for 12 hours at room temperature, the reaction mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO4. The solvent was removed by a rotary evaporator and the residue was recrystallized from MC and MeOH to obtain 62 g (63percent) of Compound A-4.

Reference： [1] Patent: EP2857395, 2015, A1, . Location in patent: Paragraph 0071
[2] Patent: WO2011/99718, 2011, A1, . Location in patent: Page/Page column 15
[3] RSC Advances, 2015, vol. 5, # 35, p. 27235 - 27241
[4] Patent: CN103819455, 2016, B, . Location in patent: Paragraph 0053; 0060; 0061
[5] Patent: KR2015/34146, 2015, A, . Location in patent: Paragraph 0045; 0052; 0053
[6] Macromolecules, 2010, vol. 43, # 8, p. 3613 - 3623

[ 185626-73-7 ] Synthesis Path-Downstream 1~32

1
[ 76-86-8 ]
[ 108-36-1 ]
[ 185626-73-7 ]

Yield	Reaction Conditions	Operation in experiment
95%		1,3-Dibromobenzene 20 g (84.77 mmol) was dissolved in THF 500 mL, and then cooled to a temperature of -78. n-BuLi 2.5M 33.9 mL(84.77 mmol) was slowly added thereinto, and then stirred at a temperature of -78 for 1 hour. Chlorotriphenylsilane ((C6H5)3SiCl) 29.9 g was dissolved in THF 100 mL, and this solution was added into the above reaction mixture. The resultant mixture was slowly warmed to room temperature, and stirred for 12 hours. Then, extraction with EA, wash with distilled water and aqueous NaCl solution, drying over MgSO4, distillation under reduced pressure, and recrystallization with MC-MeOH in the ratio of 1:10, were sequentially performed, thereby obtaining Compound 8-1 18 g(95 %).
87%		Preparation of Compound 2-3 After 1,3-dibromobenzene (11.2 g, 47 mmol) was dissolved in THF (200 mL), the mixture was cooled to -78 C. After slowly adding n-BuLi (19 mL, 2.5M in hexane, 70.5 mmol), the mixture was stirred for 1 hour. Solution that TPS-Cl (20 g, 56.8 mmol) was dissolved in THF (25 mL) was slowly added. After slowly increasing temperature, the mixture was stirred at room temperature for one day. Upon completion of the reaction, H2O was added and the mixture was extracted with EA/H2O. After removing moisture with MgSO4 and performing distillation under reduced pressure, Compound 2-3 (17 g, 87%) was obtained by column(MC/Hexane) separation.
63%		1,3-dibromobenzene (20g, 84. 77mmol) was added to the reaction vessel, and nitrogen atmosphere was created in a vacuum state. After addition of tetrahydrofuran (500mL), the mixture was stirred at -78 C for 10 min. After slowly added N-BuLi (2. 5M) (33. 9mL, 84. 77mmol), the mixture was stirred at -78 C for 1 hour. Chloro triphenylsilyl(29. 9g, 107. 72mmol) was dissolved THF (lOOmL) in, and slowly added the mixture. After stirring for 12 hours at room temperature, the reaction was complete and the mixture was washed with distilled water. Extracted with EA, and the organic layer was dried with MgS04, using a rotary evaporatorAnd slowly added to the solvent. To give compound A-4 (62g, 63%) was recrystallized from MC and Mu0Eta

63%		20g (84.77mmol) 1,3-dibromobenzene in a reaction vessel to create a vacuum with nitrogen atmosphere was added 500mL THF was stirred at -78 C 10 minutes. 33.9 mL (84.77 mmol) of n-BuLi (2.5 M) was slowly added thereto, followed by stirring at -78 C for 1 hour. 29.9 g (107.72 mmol) of chlorotriphenylsilane was dissolved in 100 mL of THF and then slowly added. After stirring for 12 hours at room temperature, the reaction mixture was washed with distilled water and extracted with EA. The organic layer was dried over MgSO4. The solvent was removed by a rotary evaporator and the residue was recrystallized from MC and MeOH to obtain 62 g (63%) of Compound A-4.
60%		Under a nitrogen atmosphere,1,3-Dibromobenzene (5.12 ml, 42.39 mmol) was dissolved in THF (200 mL).The reaction temperature was lowered to about -78 C.N-BuLi (2.5 M in hexanes, 17 ml, 42.5 mmol) was slowly added dropwise to the reaction mixture.It was then stirred at the same temperature for about 1 hour.A solution of triphenylsilyl chloride (15 g, 50.87 mmol, THF (50 ml)) was slowly added dropwise to the reaction mixture.Stir at about -78 C for about 1 hour,Then, the reaction mixture was stirred at room temperature for about 12 hours.A 20% NH4Cl solution was added to the reaction mixture to terminate the reaction.The reaction mixture was extracted with EA.The organic layer was separated, dried over MgSO 4 to remove water and separated by column chromatography (hexane).To give the intermediate compound (12) (10.57g, 60% yield).

Reference： [1]Patent: EP2857395,2015,A1 .Location in patent: Paragraph 0071
[2]Patent: WO2011/99718,2011,A1 .Location in patent: Page/Page column 15
[3]RSC Advances,2015,vol. 5,p. 27235 - 27241
[4]Patent: CN103819455,2016,B .Location in patent: Paragraph 0053; 0060; 0061
[5]Patent: KR2015/34146,2015,A .Location in patent: Paragraph 0045; 0052; 0053
[6]Macromolecules,2010,vol. 43,p. 3613 - 3623
[7]Patent: CN109320449,2019,A .Location in patent: Paragraph 0221; 0222; 0223; 0224

2
[ 185626-73-7 ]
[ 1329603-61-3 ]

Reference： [1]Patent: WO2011/99718,2011,A1

3
[ 185626-73-7 ]
[ 1253912-58-1 ]

Yield	Reaction Conditions	Operation in experiment
66%		Preparation of Compound 2-4After Compound 2-3 (17.3 g, 41.8 mmol) was dissolved in THF (200 mL), the mixture was cooled to -78 C. After slowly adding n-BuLi (20 mL, 2.5M in hexane, 50 mmol), the mixture was stirred for 1 hour. Trimethyl borate (7 mL, 67 mmol) was slowly added thereto and temperature was slowly increased. The mixture was stirred at room temperature for one day. Upon completion of the reaction, 2M HCl was added and the mixture was extracted with EA/H2O. After removing moisture with MgSO4 and performing distillation under reduced pressure, Compound 2-4 (10.5 g, 66%) was obtained by column(MC/Hexane) separation.

Reference： [1]Patent: WO2011/99718,2011,A1 .Location in patent: Page/Page column 15

4
[ 185626-73-7 ]
[ 1329604-11-6 ]

Reference： [1]Patent: WO2011/99718,2011,A1

5
[ 185626-73-7 ]
[ 633-70-5 ]
C₆₂H₄₆Br₂O₂Si₂ [ No CAS ]

Reference： [1]Macromolecules,2010,vol. 43,p. 3613 - 3623

6
[ 185626-73-7 ]
[ 111928-42-8 ]
1-N-(naphthalen-2-yl)-1-N,4-N-diphenyl-4-N-(3-(triphenylsilyl)phenyl)naphthalene-1,4-diamine [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 27235 - 27241

7
[ 185626-73-7 ]
[ 1253911-56-6 ]

Reference： [1]Patent: EP2857395,2015,A1

8
[ 185626-73-7 ]
[ 1357066-10-4 ]

Reference： [1]Patent: EP2857395,2015,A1

9
[ 121-43-7 ]
[ 185626-73-7 ]
[ 1253912-58-1 ]

Yield	Reaction Conditions	Operation in experiment
35%		Compound 8-1 20 g (90.06 mmol) was dissolved in THF 600 mL, and then cooled to - 78. n-BuLi 2.5M 43.2 mL(108.08 mmol) was slowly added thereinto, and then stirred at a temperature of -78 for 1 hour. Trimethylborate 16.06 mL(144.11 mmol) was added thereinto. The resultant mixture was slowly warmed to room temperature, and stirred for 12 hours. Then, extraction with EA, wash with distilled water and aqueous NaCl solution, drying over MgSO4, distillation under reduced pressure, and recrystallization with MC-MeOH in the ratio of 1:10, were sequentially performed, thereby obtaining Compound 8-2 12 g(35 %).

Reference： [1]Patent: EP2857395,2015,A1 .Location in patent: Paragraph 0072

10
[ 773837-37-9 ]
[ 185626-73-7 ]
copper(l) cyanide [ No CAS ]
3-triphenylsilylbenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		BB-1 (1 g, 2.4 mmol) and CuCN (0.32 g, 3.6 mmol) are suspended in DMF (12 ml) under argon and heated up to 145 C with stirring. TLC shows complete consumption of the starting material after 17 h. The reaction mixture is diluted with aqueous 1 % NaCN solution (36 ml) and stirring is continued for 1 h at 100 C. The precipitate is filtered off, washed with water and ethanol. It is dried in vacuo at 60 C and crude product BB-11 (896 mg, 2.1 mmol, 86%) is obtained with 83% HPLC purity and is used in the next reaction without further purification. 1 H NMR (DMSO-cfe, 300 MHz), delta [ppm] = 7.47-7.56 (m, 15H, -SiPh3), 7.67-7.72 (m, 1 H, H 5), 7.80-7.86 (m, 2H, H-2 + H-6), 7.99-8.01 (m, 1 H, H-4).

Reference： [1]Patent: WO2015/114102,2015,A1 .Location in patent: Page/Page column 66-67

11
[ 185626-73-7 ]
[ 1442648-11-4 ]
C₆₀H₄₂N₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium phosphate; copper(l) iodide; ethylenediamine; In toluene; at 120℃; for 4h;	After introducing compound 1-2 (9.3g, 19.26 mmol), <strong>[185626-73-7](3-bromophenyl)triphenylsilane</strong> (12 g, 28.89 mmol), copper(I) iodide (1.8g, 9.63 mmol), ethylene diamine (1.3mL, 19.26 mmol), potassium phosphate (lOg, 48.15 mmol), and toluene (lOOmL) into a reaction vessel, the mixture was stirred at 120C for 4 hours. After completion of the reaction, the mixture was washed with distilled water, and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The resultant was subjected to column chromatography to obtain compound C-8 (lOg, yield: 64%).

Reference： [1]Patent: WO2016/93584,2016,A1 .Location in patent: Page/Page column 23

12
[ 1060735-14-9 ]
[ 185626-73-7 ]
C₅₄H₃₈N₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19%	With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 120℃; for 4h;	After introducing 9-phenyl-9H,9?H-3 ,3?-bicarbazole(8g, 19.58 mmol), <strong>[185626-73-7](3-bromophenyl)triphenylsilane</strong> (9.8 g, 23.50 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.9g, 1.00 mmol), tri-t-butyl phosphine (0.9 mL, 1.96 mmol), sodium tert-butoxide (2.8g, 29.37 mmol), and toluene (lOOmL) into a reaction vessel, the mixture was stirred at 120C for 4 hours. After completion of the reaction, the mixture was washed with distilled water, and extracted with ethyl acetate. The obtained organic layer was dried with magnesium sulfate, and the solvent was removed therefrom by a rotary evaporator. The resultant was subjected to column chromatography to obtain compound C-2 (2.7g, yield: 19%).

Reference： [1]Patent: WO2016/93584,2016,A1 .Location in patent: Page/Page column 24

13
[ 185626-73-7 ]
C₄₉H₃₇N₃Si [ No CAS ]

Reference： [1]Patent: CN103819455,2016,B
[2]Patent: KR2015/34146,2015,A

14
[ 150-46-9 ]
[ 185626-73-7 ]
[ 1253912-58-1 ]

Yield	Reaction Conditions	Operation in experiment
45%		Compound Alpha-4 (22. 5g, 0.10mol) was added to the reaction vessel, and nitrogen gas is formed in a vacuum state atmosphere. After addition of tetrahydrofuran (1. 3L), at -78 C the mixture was stirred for 10 minutes. The n-BuLi (2. 5M)(48. 6mL, 0. 12ml) was slowly added to the reaction mixture, and the mixture was stirred at -78C 1 hour. Was slowly added triethyl borate(18mL, 0. 16mmol). After stirring at room temperature for 12 hours, and the completion of the reaction the mixture was washed with distilled water. Extracted with EAAfter the organic layer was taken and dried MgS04, the solvent was removed using a rotary evaporator. The residue was purified by column chromatography to give compoundComposition (A-5) (10g, 45%)
45%		22.5 g (0.10 mol) of the compound A-4 was placed in a reaction vessel and made into a nitrogen atmosphere in a vacuum state, THF (1.3 L) was added thereto and the mixture was stirred at -78 C for 10 minutes. 48.6 mL (0.12 mol) of n-BuLi (2.5 M) was slowly added thereto, followed by stirring at -78 C for 1 hour. 18 mL (0.16 mmol) of triethylborate was slowly added. After stirring at room temperature for 12 hours. After the reaction was completed, the reaction mixture was washed with distilled water and extracted with EA. The organic layer was dried with MgSO4. The solvent was removed using a rotary evaporator, and the residue was purified by column to obtain 10 g (45%) of Compound A-5.

Reference： [1]Patent: CN103819455,2016,B .Location in patent: Paragraph 0053; 0062; 0063
[2]Patent: KR2015/34146,2015,A .Location in patent: Paragraph 0045; 0054; 0055

15
[ 185626-73-7 ]
C₃₀H₂₂BrN₃ [ No CAS ]
C₅₄H₄₁N₃Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%		General procedure: Prepare the format reagent, 3g of 2-chloro-4,6-diphenyl-1,3,5-triazine,3.5 g of magnesium was added to 30 ml of tetrahydrofuran, and the temperature was raised to reflux reaction.27 g of 2-chloro-4,6-diphenyl-1,3,5-triazine dissolved in 270 ml of tetrahydrofuran was added under reflux.After the addition is completed, the temperature is kept at reflux for about 1 hour, and it is reserved.Add 39.5g of 2,7-dibromo-9,9-dimethylhydrazine to another three-necked bottle.200ml tetrahydrofuran was stirred evenly, protected by nitrogen, and cooled to -5 C.Transfer the prepared format reagent to the dropping funnel and slowly add it.Keep the temperature of the system not more than 10 C, stir for 30 min after the addition, and then slowly increase to room temperature.After 5 hours, the reaction of the starting material was completed, and a saturated aqueous solution of ammonium chloride was added dropwise to the reaction solution.After stirring for 5 min, dichloromethane was extracted, and the organic phase was dried under reduced pressure.The residue was subjected to column chromatography to give 27.7 g of Intermediate 1-1 (yield 49%).

Reference： [1]Patent: CN108409773,2018,A .Location in patent: Paragraph 0083; 0108; 0110; 0119

16
[ 185626-73-7 ]
C₃₀H₂₁NOSi [ No CAS ]
C₅₄H₃₉NOSi₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With 1,10-Phenanthroline; potassium carbonate; In N,N-dimethyl-formamide; for 24h;Reflux;	2.4 g of Intermediate 1-3, 2.9 g of <strong>[185626-73-7](3-bromophenyl)triphenylsilane</strong>, 0.5 g of copper iodide, 0.5 g of 1,10-phenanthroline, and 2 g of potassium carbonate were dissolved in 30 ml of DMF, followed by refluxing for about 24 hours. After finishing the reaction, the reaction solution was extracted with ethyl acetate, a collected organic layer was dried with magnesium sulfate, and solvents were evaporated. The residue thus obtained was separated by silica gel column chromatography to obtain 1.7 g (yield: 62%) of Compound 17. Compound 17 was identified with LC-MS and 1H-NMR.

Reference： [1]Patent: US2018/334468,2018,A1 .Location in patent: Paragraph 0162; 0163

17
[ 185626-73-7 ]
C₃₀H₂₃NO₂Si [ No CAS ]

Reference： [1]Patent: CN109320449,2019,A

18
[ 185626-73-7 ]
C₃₀H₂₃NSi [ No CAS ]

Reference： [1]Patent: CN109320449,2019,A

19
[ 185626-73-7 ]
C₄₈H₃₃FN₂Si [ No CAS ]

Reference： [1]Patent: CN109320449,2019,A

20
[ 185626-73-7 ]
C₆₀H₄₁N₃Si [ No CAS ]

Reference： [1]Patent: CN109320449,2019,A

21
[ 185626-73-7 ]
[ 73183-34-3 ]
triphenyl [3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 60 - 80℃; for 14h;Inert atmosphere;	The intermediate compound (12) (6.85 g, 16.5 mmol), under a nitrogen atmosphere,Bis (pinacolato) diboron (6.28g, 16.5mmol),Potassium acetate (3.56 g, 36.27 mmol)Mixed with 1,4-dioxane (40ml),It is then stirred at about 60 C for about 15 minutes.Pd(dppf)CH2Cl2 (0.18 g, 0.25 mmol) was added to the reaction mixture.It was then stirred at about 80 C for about 14 hours.The reaction mixture was cooled to room temperature, extracted with toluene, dried over MgSO 4 to remove water, and separated by column chromatography (hexane: EA = 5:1, v/v).The intermediate compound (13) (6.34 g, yield: 81%) was obtained.

Reference： [1]Patent: CN109320449,2019,A .Location in patent: Paragraph 0221; 0222; 0225; 0226

22
[ 185626-73-7 ]
[ 5570-18-3 ]
[ 2374195-59-0 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In tetrahydrofuran; water at 80℃; for 8h; Inert atmosphere;	1.1 (1) Synthesis of Intermediate 1 Intermediate 1-1 (7 g, 16.85 mmol), Intermediate 1-2 (2.77 g, 20.22 mol), Pd(PPh3)4 (973 mg, 0.84 mmol) and K2CO3 (7 g, 50.55 mmol) were introduced to a 500 mL round bottom flask. Under a nitrogen condition, tetrahydrofuran (THF) (200 ml) and H2O (50 ml) were introduced thereto, and the result was stirred for 8 hours after raising the temperature to 80° C. After lowering the temperature, the material was extracted using dichloromethane (DCM) and water, and the result was stirred after introducing MgSO4 and acid clay. After passing the result through silica gel, the solvent was removed. The material was separated through column chromatography (methyl chloride/hexane).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US2020/270279, 2020, A1 Location in patent: Paragraph 0126; 0127

23
[ 185626-73-7 ]
[ 2374195-59-0 ]
[ 2374195-60-3 ]

Yield	Reaction Conditions	Operation in experiment
	With bis(tri-t-butylphosphine)palladium⁽⁰⁾; sodium t-butanolate In toluene at 100℃; for 2h; Inert atmosphere; Darkness;	1.2 (2) Synthesis of Intermediate 2 Intermediate 1 (3 g, 7.02 mmol), Intermediate 1-1 (2.64 g, 6.38 mmol) and sodium tert-butoxide (NaOtBu) (920 mg, 9.57 mmol) were introduced to a 250 ml round bottom flask. Under a nitrogen condition, toluene (100 ml) was introduced thereto, and the temperature was raised to 100° C. After introducing Pd(P(tBu3))2 (163 mg, 0.32 mmol) to the round bottom flask and blocking the light, the result was stirred for 2 hours. After lowering the temperature, the material was extracted using dichloromethane (DCM) and water, and the result was stirred after introducing MgSO4 and acid clay. After passing the result through silica gel, the solvent was removed. The material was separated through column chromatography (methyl chloride/hexane).

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US2020/270279, 2020, A1 Location in patent: Page/Page column 0126; 0128; 0129

24
[ 185626-73-7 ]
[ 2230595-79-4 ]
[ 2640573-76-6 ]

Yield	Reaction Conditions	Operation in experiment
83%	With palladium diacetate; potassium carbonate; XPhos In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;	1 Synthesis Example-1 Under an argon atmosphere, 2,4-diphenyl-6- [3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1,1': 2', 1' '-Terphenyl-3-yl] -1,3,5-triazine (2.74 g, 4.7 mmol), 3-bromo-1-triphenylsilylbenzene (2.18 g, 5.1 mmol), palladium acetate (2.74 g, 4.7 mmol) 60 mg, 0.29 mmol), and 2-dicyclohexylphosphino-2', 4', 6'-triisopropylbiphenyl (252 mg, 0.58 mmol) were suspended in THF (60 mL). After adding a 2M-potassium carbonate aqueous solution (8 mL) to this suspension, the mixture was heated under reflux for 24 hours. After allowing to cool, water and methanol were added to the reaction mixture, and the resulting solid was collected by filtration. By washing the obtained solid with toluene, the desired 2,4-diphenyl-6- [3-triphenylsilyl-1,1': 5', 1'': 2'', 1'''- Quaterphenyl-3'-yl] -1,3,5-triazine (1-41) was obtained (3.09 g, 3.88 mmol, 83%).

Reference： [1]Current Patent Assignee: TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE - JP2021/66689, 2021, A Location in patent: Paragraph 0154-0157

25
[ 185626-73-7 ]
[ 1802232-96-7 ]
[ 2558185-73-0 ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; potassium carbonate; XPhos In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;	11 Synthesis Example-11 Under an argon atmosphere, 4,6-diphenyl-2- [3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -biphenyl-5'-yl] -1, 3,5-Triazine (2.76 g, 5.42 mmol), 3-Bromo-1-triphenylsilylbenzene (2.37 g, 5.76 mmol), Palladium acetate (60 mg, 0.29 mmol), 2-dicyclohexylphosphino -2', 4', 6'-triisopropylbiphenyl (252 mg, 0.58 mmol) was suspended in THF (60 mL). After adding a 2M-potassium carbonate aqueous solution (8 mL) to this suspension, the mixture was heated under reflux for 24 hours. After allowing to cool, water and methanol were added to the reaction mixture. By filtering the resulting solid and recrystallizing it with toluene, 4,6-diphenyl-2- [3-triphenylsilyl- (1,1': 3', 1'')-terphenyl-3' A white solid of'-yl] -1,3,5-triazine (1-171) was obtained (2.68 g, 70%).

Reference： [1]Current Patent Assignee: TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE - JP2021/66689, 2021, A Location in patent: Paragraph 0189-0191

26
[ 185626-73-7 ]
[ 1518823-39-6 ]
[ 2640573-77-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With palladium diacetate; potassium carbonate; XPhos In tetrahydrofuran; water for 24h; Inert atmosphere; Reflux;	2 Synthesis Example-2 Under an argon atmosphere, 2,4-diphenyl-6- [3- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -biphenyl-5-yl] -1,3 , 5-Triazine (2.69 g, 5.3 mmol), 3-Bromo-1-triphenylsilylbenzene (2.40 g, 5.8 mmol), Palladium acetate (60 mg, 0.29 mmol), 2-Dicyclohexylphosphino- 2', 4', 6'-triisopropylbiphenyl (252 mg, 0.58 mmol) was suspended in THF (60 mL). After adding a 2M-potassium carbonate aqueous solution (8 mL) to this suspension, the mixture was heated under reflux for 24 hours. After allowing to cool, water and methanol were added to the reaction mixture. The precipitated solid was collected by filtration and washed with toluene to obtain the desired 2,4-diphenyl-6- [3-triphenylsilyl-1,1': 5', 1 "-terphenyl-3'-. Ill] -1,3,5-triazine (1-40) was obtained (2.66 g, 3.7 mmol, 70%).

Reference： [1]Current Patent Assignee: TOSOH CORPORATION; SAGAMI CHEMICAL RESEARCH INSTITUTE - JP2021/66689, 2021, A Location in patent: Paragraph 0158-0160

27
[ 185626-73-7 ]
[ 1391041-75-0 ]

Yield	Reaction Conditions	Operation in experiment
64.97 g	With n-hexyllithium In tetrahydrofuran; hexane at -78℃; for 1.08333h;	2 Step 2 Add (3-bromophenyl)triphenylsilane (72.0g, 173mmol) and THF (1576ml) to a 5L flask. The resulting reaction mixture was stirred and cooled to -78°C. A solution of hexyllithium in hexane (2.3M, 113ml, 260mmol) was added over 20 minutes and stirred for 45 minutes. Then slowly add a solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (60.1ml, 295mmol) in THF (158ml), And the reaction mixture was warmed to room temperature and stirred overnight (about 16 hours). The reaction mixture was quenched with ice cold water (1 L) and the organic layer was separated. The aqueous layer was extracted with EtOAc (2×700 mL), and the combined organic layer was dried over Na 2 SO 4, filtered and concentrated. The off-white solid was wet-milled with heptane (500 mL) to obtain triphenyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2)-Yl)phenyl)silane as a white solid (64.97g).

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - CN112707923, 2021, A Location in patent: Paragraph 0362; 0364

28
[ 61676-62-8 ]
[ 185626-73-7 ]
[ 1391041-75-0 ]

Yield	Reaction Conditions	Operation in experiment
64.97 g	Stage #1: 3-bromophenyltriphenylsilyl chloride With n-hexyllithium In tetrahydrofuran; hexane at -78℃; for 1.08333h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 20℃; for 16h;	2 Step 2 To a 5 L flask was added (3-bromophenyl)triphenylsilane (72.0 g, 173 mmol) and THF (1576 ml). The resulting reaction mixture was stirred and cooled to -78° C. A solution of hexyllithium in hexane (2.3 M, 113 ml, 260 mmol) was added over 20 min and stirred for 45 min. A solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (60.1 ml, 295 mmol) in THF (158 ml) was then added slowly and the reaction mixture was allowed to warm to room temperature and stirred overnight (˜16 hours). The reaction mixture was quenched with ice-cold water (1 L) and the organic layer was separated. The aqueous layer was extracted with EtOAc (2*700 mL), the combined organic layer was dried over Na2SO4, filtered, and concentrated. The off-white solid was triturated with heptane (500 mL) to give a triphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)silane (64.97 g) as a white solid.

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - US2021/122765, 2021, A1 Location in patent: Paragraph 0194; 0196

29
[ 185626-73-7 ]
[ 86-74-8 ]
[ 944465-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate	1 Synthesis of Intermediate 3-1 1 mole eq. of carbazole and 1 mole eq. of (3-bromophenyl)triphenylsilane were reacted with 0.04 mole eq. of tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3), 0.08 mole eq. of tri-tert-butylphosphine (P(tBu)3), and 1.5 mole eq. of sodium tert-butoxide (NaOtBu) to obtain Intermediate 3-1. Intermediate 3-1 was identified by liquid chromatography-mass spectrometry (LC-MS). C36H27NSi M+1:502.21
	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 130℃;	1 Synthesis of Intermediate A-1 To a round-bottom flask, (3-bromophenyl)triphenylsilane (10 g, 1 eq), 9H-carbazole (4.4 g, 1 eq), sodium tert-butoxide (3.5 g, 1.5 eq), tris(dibenzylideneacetone)dipalladium(0) (0.88 g, 0.04 eq), tri-tert-butylphosphine (0.8 ml, 0.08 eq), and toluene (120 ml) were added and refluxed (about 130° C.) overnight while stirring. After finishing the reaction, silica filtration was performed with methylene chloride, and solvents were removed therefrom. The crude product thus obtained was separated by column chromatography using hexane:methylene chloride (4:1), solidified using methanol, filtered and dried to synthesize Intermediate A-1 (yield 91%). (0261) C36H27NSi [M]+: calcd: 502.19, measured: 501
	With n-butyllithium at 70℃;	1.6.1 1) Synthesis of Intermediate 70-1 9H-carbazole (CAS : 86-74-8) and n-BuLi were reacted, and (3-bromophenyl)triphenylsilane (CAS : 185626-73-7) was added thereto, followed by stirring at about 70° C. overnight to obtain Intermediate 70-1. Intermediate 70-1 was identified by LC-MS.C36H27NSi M+1: 502.20

77 %

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 110℃;

1 Synthesis of Intermediate 1-3 20 g of carbazole, 49.69 g of (3-bromophenyl)triphenylsilane (CAS=185626-73-7), 21 g of NaOtBu, 4.38 g of Pd2(dba)3, and 2.15 mL of tri-tert-butylphosphine 50% xylene solution (TTBuP-50T) were dissolved in 600 mL of toluene solvent, and then, stirred at a temperature of 110° C. for 12 hours. After the reaction was completed, the reaction solution was extracted and the obtained organic layer was dried. The residue was isolated and purified by column chromatography to obtain 46 g (yield of 77%) of Intermediate 1-3. Intermediate 1-3 was confirmed by LC-MS. (C36H27NSi: M+1 501.70)

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - US2021/376262, 2021, A1 Location in patent: Paragraph 0368-0370
[2]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2022/109121, 2022, A1 Location in patent: Paragraph 0259; 0260; 0261
[3]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - US2023/225192, 2023, A1 Location in patent: Paragraph 0232; 0273-0275
[4]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2023/127262, 2023, A1 Location in patent: Paragraph 0393; 0396

30
[ 185626-73-7 ]
[ 18628-07-4 ]
[ 2665768-26-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	With dicyclohexyl({2’,6’-dimethoxy-[1,1‘-biphenyl]-2-yl})phosphane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium tertiary butoxide In 5,5-dimethyl-1,3-cyclohexadiene at 150℃; Inert atmosphere;
49%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium tertiary butoxide In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 120℃; for 12h;	2 Synthesis Example 2 (Compound 4) 2.9 g of (3-bromophenyl)triphenylsilane and 2.8 g of 9H-3,9′-bicarbazole were added to a reaction vessel, and 0.3 g of Pd2(dba)3, 0.12 mL of P(tBu3) (50 wt % in xylene), 1.2 g of NaOtBu, and 50 mL of toluene were added dropwise thereto. Then the reaction temperature was raised to 120° C. and refluxed for 12 hours. An organic layer was extracted from the resulting mixture using ethyl acetate and dried using magnesium sulfate, and the solvent was evaporated to obtain residue. The residue was subjected to silica gel column chromatography for separation and purification to thereby obtain 2.3 g of Compound 4 (yield: 49%). The results of LC-MS and 1H-NMR on Compound 4 are shown in Table 1.

Reference： [1]Kim, Dong Jun; Baek, Seung-Hyun; Kim, Woo-Sam; Ahn, Kwang-Hyun; Lee, Jeong-Hwan [Journal of Materials Chemistry C, 2022, vol. 10, # 22, p. 8602 - 8608]
[2]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - US2021/376262, 2021, A1 Location in patent: Paragraph 0374-0375

31
[ 121-43-7 ]
[ 185626-73-7 ]
[ CAS Unavailable ]
[ 1253912-58-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: (3-bromophenyl)triphenylsilane With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.166667h; Stage #2: Trimethyl borate In tetrahydrofuran; hexane Stage #3: water monomer With ammonia hydrochloride In tetrahydrofuran; hexane	4 Synthesis of Intermediate A-7 To a round-bottom flask, (3-bromophenyl)triphenylsilane (1 eq) was added, and THF (150 ml) was added. At about -78° C., n-BuLi (2 M in hexane, 17 ml, 1.2 eq) was slowly added thereto dropwisely. After about 40 minutes, trimethyl borate (5.75 ml, 1.5 eq) was slowly added thereto dropwisely, and then, the temperature was slowly elevated and stirred overnight. The reaction was quenched using water and a NH4Cl solution, and the resultant product was washed with ethyl acetate/H2O, dried with MgSO4, and then separated by column chromatography using methylene chloride:ethyl acetate to obtain Intermediate A-7 (yield 77%).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2022/109121, 2022, A1 Location in patent: Paragraph 0278-0279

32
[ 185626-73-7 ]
[ 102113-98-4 ]
[ 2055237-66-4 ]

Yield	Reaction Conditions	Operation in experiment
87 %	With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate In toluene at 100℃; Inert atmosphere;	Synthesis of Compound 13 Compound 13 was synthesized as an example compound.Under an argon atmosphere, 4.7 g of 3-bromotetraphenylsilane, 3.5 g of bisbiphenylylamine, 60 ml of toluene, 3.2 g of sodium tert-butoxide, and bis(dibenzylideneacetonato)palladium are placed in a 200 mL three-necked flask. 0.33 g was sequentially added, and 0.8 ml of a 2 mol/L toluene solution of tri-tert-butylphosphine prepared under an argon atmosphere was added, followed by heating under reflux at 100° C. for 10 hours.The resulting solid was purified by flash column chromatography to give 6.2 g of compound 13 as a white solid (87% yield).

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - JP2016/207885, 2016, A Location in patent: Paragraph 0071

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