Name: 57102-97-3|3-Bromo-9-ethyl-9H-carbazole|95%
Brand: Ambeed
SKU: A350026
Price: 8.0 USD
Availability: InStock
Rating: 97 (32 reviews)

1
[ 86-28-2 ]
[ 57102-97-3 ]

Reference： [1]Journal of Organic Chemistry,2019
[2]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1983 - 1994
[3]Journal of the Brazilian Chemical Society,2010,vol. 21,p. 496 - 501
[4]Journal of Materials Chemistry,2011,vol. 21,p. 9139 - 9148
[5]Dyes and Pigments,2013,vol. 99,p. 577 - 587
[6]Chemistry Letters,2011,vol. 40,p. 872 - 873
[7]Chemistry Letters,2015,vol. 44,p. 958 - 960
[8]Journal de Chimie Physique et de Physico-Chimie Biologique,1995,vol. 92,p. 823 - 826
[9]Journal of Organic Chemistry,1951,vol. 16,p. 1198,1204
[10]Dalton Transactions,2014,vol. 43,p. 13076 - 13086
[11]Heterocyclic Communications,2016,vol. 22,p. 287 - 290

2
[ 86-28-2 ]
[ 57102-97-3 ]
[ 33255-13-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium bromate; hydrogenchloride; acetic acid; potassium bromide
	With potassium bromate; water; potassium bromide
	With tetrachloromethane; N-Bromosuccinimide

With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 4.5h; Yield given. Yields of byproduct given;

Reference： [1]Buu-Hoi; Royer [Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 533,541]
[2]Meen; Gilman [Journal of Organic Chemistry, 1955, vol. 20, p. 73,78] Gilman; Kirby [Journal of Organic Chemistry, 1936, vol. 1, p. 146,152]
[3]Buu-Hoi; Royer [Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 533,541]
[4]Smith, Keith; Martin James; Mistry, Anil G.; Bye, Martin R.; John Faulkner [Tetrahedron, 1992, vol. 48, # 36, p. 7479 - 7488]

3
[ 57102-97-3 ]
[ 57102-98-4 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; diethyl ether; benzene Anschliessend Behandeln mit festem CO₂;

Reference： [1]Gilman; Spatz [Journal of the American Chemical Society, 1941, vol. 63, p. 1553,1554] Gilman; Kirby [Journal of Organic Chemistry, 1936, vol. 1, p. 146,152]

4
[ 86-28-2 ]
[ 57102-97-3 ]
[ 33255-13-9 ]
[ 144434-81-1 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; silica gel In dichloromethane at 18℃; for 6h; Yield given. Yields of byproduct given;

Reference： [1]Smith, Keith; Martin James; Mistry, Anil G.; Bye, Martin R.; John Faulkner [Tetrahedron, 1992, vol. 48, # 36, p. 7479 - 7488]

5
[ 57102-97-3 ]
[ 20466-00-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With [2,2]bipyridinyl; nickel dibromide; zinc In N,N-dimethyl-formamide

Reference： [1]Kham, K.; Sadki, S.; Chevrot, C. [Journal de Chimie Physique et de Physico-Chimie Biologique, 1995, vol. 92, # 4, p. 823 - 826]

6
[ 57102-97-3 ]
[ 33513-42-7 ]
[ 24301-72-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With trichlorophosphate for 0.03h; microwave irradiation;

Reference： [1]Nagarajan, Rajagopal; Perumal, Paramasivan T. [Synthetic Communications, 2004, vol. 34, # 12, p. 2127 - 2133]

7
[ 109-04-6 ]
[ 57102-97-3 ]
[ 888949-97-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-pyridine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.75h; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at 20℃; for 1.5h; Stage #3: 3-bromo-9-ethyl-9H-carbazole In tetrahydrofuran; hexane for 16h; Heating; Further stages.;

Reference： [1]Zhang, Xiaowei; Yang, Chuluo; Chen, Liang; Zhang, Kai; Qin, Jingui [Chemistry Letters, 2006, vol. 35, # 1, p. 72 - 73]
[2]Zhang, Kai; Chen, Zhao; Yang, Chuluo; Zhang, Xiaowei; Tao, Youtian; Duan, Lian; Chen, Liang; Zhu, Linna; Qin, Jingui; Cao, Yong [Journal of Materials Chemistry, 2007, vol. 17, # 32, p. 3451 - 3460]

8
[ 57102-97-3 ]
[ 62-53-3 ]
[ 436800-48-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With tri-tert-butyl phosphine; sodium t-butanolate In toluene at 80℃;

Reference： [1]Justin Thomas; Lin; Tao; Ko [Journal of the American Chemical Society, 2001, vol. 123, # 38, p. 9404 - 9411]

9
[ 57102-97-3 ]
N,N'-bis(9-ethyl-9H-carbazol-3-yl)-9-N,N'-triphenyl-9H-carbazole-3,6-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 86 percent / (t-Bu)3P; t-BuONa / Pd(dba)3 / toluene / 80 °C 2: 74 percent / Pd(dba)2; (t-Bu)3; tBuONa / toluene / 80 °C

Reference： [1]Justin Thomas; Lin; Tao; Ko [Journal of the American Chemical Society, 2001, vol. 123, # 38, p. 9404 - 9411]

10
[ 86-74-8 ]
[ 57102-97-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetone; aqueous KOH-solution 2: tetrachloromethane; <i>N</i>-bromo-succinimide
	Multi-step reaction with 2 steps 1: pyridine; bromine / 2 h / 0 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 60 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C

	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide 2: potassium hydroxide / acetone
	Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide 2: N-Bromosuccinimide / N,N-dimethyl-formamide
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 2 h / 0 - 20 °C 2: potassium hydroxide / N,N-dimethyl-formamide / 12 h / 80 °C
	Multi-step reaction with 2 steps 1: potassium hydroxide / N,N-dimethyl-formamide / 60 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C / Inert atmosphere; Darkness
	Multi-step reaction with 2 steps 1: N-Bromosuccinimide / N,N-dimethyl-formamide / 3 h / 0 - 20 °C 2: tetra-(n-butyl)ammonium iodide; sodium hydroxide / water / 24 h / Inert atmosphere

Reference： [1]Buu-Hoi; Royer [Recueil des Travaux Chimiques des Pays-Bas, 1947, vol. 66, p. 533,541]
[2]Reghu, Renji R.; Bisoyi, Hari Krishna; Grazulevicius, Juozas V.; Anjukandi, Padmesh; Gaidelis, Valentas; Jankauskas, Vygintas [Journal of Materials Chemistry, 2011, vol. 21, # 21, p. 7811 - 7819]
[3]Kim, Se Hun; Cho, Illhun; Sim, Mun Ki; Park, Sanghyuk; Park, Soo Young [Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148]
[4]Irgashev, Roman A.; Kim, Grigory A.; Rusinov, Gennady L.; Charushin, Valery N. [ARKIVOC, 2014, vol. 2014, # 5, p. 123 - 131]
[5]Zhang, Qiang; Wei, Huaixin; Zhai, Rongjia; Ji, Zhongling; Qi, Yu; Zhao, Xin [Heterocyclic Communications, 2016, vol. 22, # 5, p. 287 - 290]
[6]Karuppasamy, Ayyanar; Stalindurai, Kesavan; Peng, Jia-De; Ho, Kuo-Chuan; Ramalingan, Chennan [Physical Chemistry Chemical Physics, 2016, vol. 18, # 43, p. 30105 - 30116]
[7]Sivakumar, Gangala; Sasikumar, Mayarambakam; Rao, Vaidya Jayathirtha [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1983 - 1994]
[8]Enriquez-Cabrera, Alejandro; Lacroix, Pascal G.; Sasaki, Isabelle; Mallet-Ladeira, Sonia; Farfán, Norberto; Barba-Barba, Rodrigo M.; Ramos-Ortiz, Gabriel; Malfant, Isabelle [European Journal of Inorganic Chemistry, 2018, vol. 2018, # 3, p. 531 - 543]

11
[ 57102-97-3 ]
[ 30752-19-3 ]
[ 952657-51-1 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: 1-bromo-4-hexyloxylbenzene With magnesium In tetrahydrofuran for 1h; Reflux; Stage #2: 3-bromo-9-ethyl-9H-carbazole With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran Cooling with ice; Reflux;

Reference： [1]Location in patent: experimental part Koumura, Nagatoshi; Wang, Zhong-Sheng; Miyashita, Masanori; Uemura, Yu; Sekiguchi, Hiroki; Cui, Yan; Mori, Atsunori; Mori, Shogo; Hara, Kohjiro [Journal of Materials Chemistry, 2009, vol. 19, # 27, p. 4829 - 4836]

12
9,9,9'',9''-tetraoctyl-9H,9'H,9''H-2,2':7',2''-terfluoren-9'-one [ No CAS ]
[ 57102-97-3 ]
[ 1260378-66-2 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 3-bromo-9-ethyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 9,9,9'',9''-tetraoctyl-9H,9'H,9''H-2,2':7',2''-terfluoren-9'-one In tetrahydrofuran; hexane at -78 - 20℃;

Reference： [1]Lu, Yu; Zhou, Yu; Quan, Yi-Wu; Chen, Qing-Min; Chen, Run-Feng; Zhang, Zhi-Yong; Fan, Qu-Li; Huang, Wei; Ding, Jian-Fu [Organic Letters, 2011, vol. 13, # 2, p. 200 - 203]

13
[ 1592-95-6 ]
[ 75-03-6 ]
[ 57102-97-3 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetra-(n-butyl)ammonium iodide; sodium hydroxide In water for 24h; Inert atmosphere;
	With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 24h;
	With potassium hydroxide In acetone

Reference： [1]Enriquez-Cabrera, Alejandro; Lacroix, Pascal G.; Sasaki, Isabelle; Mallet-Ladeira, Sonia; Farfán, Norberto; Barba-Barba, Rodrigo M.; Ramos-Ortiz, Gabriel; Malfant, Isabelle [European Journal of Inorganic Chemistry, 2018, vol. 2018, # 3, p. 531 - 543]
[2]Location in patent: scheme or table Reghu, Renji R.; Bisoyi, Hari Krishna; Grazulevicius, Juozas V.; Anjukandi, Padmesh; Gaidelis, Valentas; Jankauskas, Vygintas [Journal of Materials Chemistry, 2011, vol. 21, # 21, p. 7811 - 7819]
[3]Irgashev, Roman A.; Kim, Grigory A.; Rusinov, Gennady L.; Charushin, Valery N. [ARKIVOC, 2014, vol. 2014, # 5, p. 123 - 131]

14
[ 57102-97-3 ]
[ 61676-62-8 ]
[ 1020657-86-6 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 3-bromo-9-ethyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -75℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	1.1 Preparation of 9-ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (1) Under a nitrogen atmosphere into a 3-bromo-ethylcarbazole (0.54 g, 1.4 mmol) and tetrahydrofuran (20 mL) into the n-butyl lithium (2.5 M, 3.4 mL) at -75°C under stirring to the three-necked flask And stirred for 1 hour. Then put the 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.64 g, 3.5 mmol) and reacted at room temperature for 24 hours. After then raising the temperature to 0 °C put HCl (4 M, 100 mL) and separate the organic layer with diethyl ether. Separate the organic layer and dry over anhydrous MgSO4 After filtration the solvent is removed. The resulting compound is a exane / methylene chloride Column: When the separation can be used as a developing solvent (5:1) Synthesis of Compound (1) in a yield of about 86%.
72%	Stage #1: 3-bromo-9-ethyl-9H-carbazole With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; for 3h;
65%	Stage #1: 3-bromo-9-ethyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃; for 12h; Inert atmosphere;	9-Ethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9Hcarbazole To a solution of 3-bromo-9-ethyl-9H-carbazole (2 g,7.33 mmol) in tetrahydrofuran (40 ml) was added n-butyl lithium (4.58 ml, 1.6 M in hexane, 7.33 mmol) dropwise at -78 °C undernitrogen atmosphere. After stirring at -78 °C for 1 h, 2-isopropoxy-4,4,5,5-tetramethyl-[1,3,2] dioxaborolane (1.47 ml, 7.33 mmol) wasadded in one portion. The resulting mixture was gradually warmedto room temperature and stirred for another 12 h. The reaction was quenched with water and extracted with dichloromethane. The crude product was purified by column chromatography on silica gelby using ethyl acetate/petroleum (1:2 by volume) as eluent toafford product as a white solid (1.53 g, yield: 65%). 1H NMR (400 MHz, CDCl3, ppm): d8.6 (s, 1H), 8.2 (d, 1H), 7.9 (d, 1H), 7.5e7.3(m, 3H), 7.25 (m, 1H), 4.3 (t, 2H), 1.45 (m, 15H). GCeMS m/zcalculated for this compound: 321.19, found 321.00.

51%	Stage #1: 3-bromo-9-ethyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at -78 - 20℃;
	With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 12h;
	With n-butyllithium In tetrahydrofuran

Reference： [1]Current Patent Assignee: PUSAN NATIONAL UNIVERSITY - KR101481147, 2015, B1 Location in patent: Paragraph 0094; 0095; 0096
[2]Sivakumar, Gangala; Sasikumar, Mayarambakam; Rao, Vaidya Jayathirtha [Journal of Heterocyclic Chemistry, 2017, vol. 54, # 3, p. 1983 - 1994]
[3]Zhang, Qingwei; Fang, Da; Jiang, Hongji; Zhang, Xinwen; Zhang, Hongmei [Organic electronics, 2015, vol. 27, p. 173 - 182]
[4]Kim, Se Hun; Cho, Illhun; Sim, Mun Ki; Park, Sanghyuk; Park, Soo Young [Journal of Materials Chemistry, 2011, vol. 21, # 25, p. 9139 - 9148]
[5]Location in patent: scheme or table Reghu, Renji R.; Bisoyi, Hari Krishna; Grazulevicius, Juozas V.; Anjukandi, Padmesh; Gaidelis, Valentas; Jankauskas, Vygintas [Journal of Materials Chemistry, 2011, vol. 21, # 21, p. 7811 - 7819]
[6]Giridhar, Thota; Cho, Woosum; Park, Juhyeon; Park, Jin-Su; Gal, Yeong-Soon; Kang, Sunwoo; Lee, Jin Yong; Jin, Sung-Ho [Journal of Materials Chemistry C, 2013, vol. 1, # 12, p. 2368 - 2378]

15
[ 872-55-9 ]
[ 57102-97-3 ]
[ 1453841-49-0 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 2-ethylthiophene With n-butyllithium In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: With zinc(II) chloride In tetrahydrofuran; hexane at 0 - 20℃; for 1h; Inert atmosphere; Stage #3: 3-bromo-9-ethyl-9H-carbazole With methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II); XPhos In tetrahydrofuran; hexane at 75℃; for 12h; Inert atmosphere;

Reference： [1]Yang, Yang; Oldenhuis, Nathan J.; Buchwald, Stephen L. [Angewandte Chemie - International Edition, 2013, vol. 52, # 2, p. 615 - 619][Angew. Chem., 2013, vol. 125, # 2, p. 643 - 647,5]

16
2-(4-hexylthiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane [ No CAS ]
[ 57102-97-3 ]
[ 1060686-46-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In toluene for 12h; Reflux; Inert atmosphere;

Reference： [1]Dohi, Toshifumi; Yamaoka, Nobutaka; Nakamura, Shota; Sumida, Kohei; Morimoto, Koji; Kita, Yasuyuki [Chemistry - A European Journal, 2013, vol. 19, # 6, p. 2067 - 2075]

17
[ 57102-97-3 ]
C₁₂H₁₉BO₂S [ No CAS ]
9-ethyl-3-(4-propylthiophen-2-yl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; toluene Reflux;

Reference： [1]Uemura, Yu; Mori, Shogo; Hara, Kohjiro; Koumura, Nagatoshi [Chemistry Letters, 2011, vol. 40, # 8, p. 872 - 873]

18
[ 57102-97-3 ]
[ 919079-93-9 ]
9-ethyl-3-(4-dodecylthiophen-2-yl)-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In 1,2-dimethoxyethane; water Reflux;

Reference： [1]Uemura, Yu; Mori, Shogo; Hara, Kohjiro; Koumura, Nagatoshi [Chemistry Letters, 2011, vol. 40, # 8, p. 872 - 873]

19
[ 57102-97-3 ]
[ 132-32-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With dicyclohexyl(2',4',6'-triisopropyl-5-methoxy-3,4,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; C₅₀H₇₀NO₄PPdS; C₅₀H₇₀NO₄PPdS; dicyclohexyl(2',4',6'-triisopropyl-4-methoxy-3,5,6-trimethyl-[1,1'-biphenyl]-2-yl)phosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;

Reference： [1]Cheung, Chi Wai; Surry, David S.; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 14, p. 3734 - 3737]

20
[ 67-56-1 ]
[ 57102-97-3 ]
[ 1383943-18-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With t-BuBrettPhos; [(2-di-tert-butylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1’-biphenyl)-2-(2’-amino-1,1‘-biphenyl)]palladium(II) methanesulfonate; sodium t-butanolate In 1,4-dioxane at 50℃; for 20h; Sealed tube; Inert atmosphere;

Reference： [1]Cheung, Chi Wai; Buchwald, Stephen L. [Organic Letters, 2013, vol. 15, # 15, p. 3998 - 4001]

21
[ 57102-97-3 ]
[ 84-65-1 ]
C₄₂H₃₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;

Reference： [1]Chang, Yu-Chen; Yeh, Shih-Chieh; Chen, Ying-Hsiao; Chen, Chin-Ti; Lee, Rong-Ho; Jeng, Ru-Jong [Dyes and Pigments, 2013, vol. 99, # 3, p. 577 - 587]

22
[ 57102-97-3 ]
[ 84-47-9 ]
C₄₆H₄₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;

Reference： [1]Chang, Yu-Chen; Yeh, Shih-Chieh; Chen, Ying-Hsiao; Chen, Chin-Ti; Lee, Rong-Ho; Jeng, Ru-Jong [Dyes and Pigments, 2013, vol. 99, # 3, p. 577 - 587]

23
[ 57102-97-3 ]
C₅₄H₄₂N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: palladium diacetate / toluene / 48 h / 120 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

Reference： [1]Chang, Yu-Chen; Yeh, Shih-Chieh; Chen, Ying-Hsiao; Chen, Chin-Ti; Lee, Rong-Ho; Jeng, Ru-Jong [Dyes and Pigments, 2013, vol. 99, # 3, p. 577 - 587]

24
[ 57102-97-3 ]
C₅₈H₅₀N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: palladium diacetate / toluene / 48 h / 120 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere

Reference： [1]Chang, Yu-Chen; Yeh, Shih-Chieh; Chen, Ying-Hsiao; Chen, Chin-Ti; Lee, Rong-Ho; Jeng, Ru-Jong [Dyes and Pigments, 2013, vol. 99, # 3, p. 577 - 587]

25
[ 57102-97-3 ]
[ 1095194-83-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C / Inert atmosphere 2.1: palladium diacetate / toluene / 48 h / 120 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: potassium acetate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 18 h / 110 °C / Inert atmosphere 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / tetrahydrofuran / 18 h / 80 °C

Reference： [1]Chang, Yu-Chen; Yeh, Shih-Chieh; Chen, Ying-Hsiao; Chen, Chin-Ti; Lee, Rong-Ho; Jeng, Ru-Jong [Dyes and Pigments, 2013, vol. 99, # 3, p. 577 - 587]
[2]Joung, Kuk Soung; Kim, Kyu Sung; Kim, Seung Uk; Tak, So Hyun; Yu, Jae-Woong [Organic electronics, 2022, vol. 100]

26
[ 57102-97-3 ]
[ 1461-22-9 ]
[ 1380428-99-8 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 3-bromo-9-ethyl-9H-carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;

Reference： [1]Chang, Yu-Chen; Yeh, Shih-Chieh; Chen, Ying-Hsiao; Chen, Chin-Ti; Lee, Rong-Ho; Jeng, Ru-Jong [Dyes and Pigments, 2013, vol. 99, # 3, p. 577 - 587]

27
[ 57102-97-3 ]
C₁₀H₁₇BrZn*LiCl [ No CAS ]
3-(3,7-dimethylocta-2,6-dien-1-yl)-9-ethyl-9H-carbazole [ No CAS ]
3-(3,7-dimethylocta-2,6-dien-1-yl)-9-ethyl-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50 % de	With 2′-(dicyclohexylphophanyl)-N₂,N₂,N₆,N₆-tetramethyl[1,1′-biphenyl]-2,6-diamine; [(2-dicyclohexylphosphino-2’,6’-bis(N,N-dimethylamino)-1,1‘-biphenyl)-2-(2’-amino-1,1’-biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Overall yield = 93 %; Overall yield = 154 mg;

Reference： [1]Yang, Yang; Mustard, Thomas J. L.; Cheong, Paul Ha-Yeon; Buchwald, Stephen L. [Angewandte Chemie - International Edition, 2013, vol. 52, # 52, p. 14098 - 14102][Angew. Chem., 2013, vol. 125, # 52, p. 14348 - 14352,5]

28
[ 57102-97-3 ]
[ 175361-81-6 ]
[ 1039452-25-9 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 618 - 629

29
[ 57102-97-3 ]
5-(9’-ethylcarbazol-3’-yl)thiophene-2-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: n-butyllithium / 1,2-dimethoxyethane 2: hydrogenchloride / water 3: potassium phosphate; trans-diacetylpalladium(II) bis(dicyclohexylamine) / methanol / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 14 h / Inert atmosphere; Reflux 2: trichlorophosphate / 1,2-dichloro-ethane / 70 °C / Inert atmosphere

Reference： [1]Irgashev, Roman A.; Kim, Grigory A.; Rusinov, Gennady L.; Charushin, Valery N. [ARKIVOC, 2014, vol. 2014, # 5, p. 123 - 131]
[2]Kono, Takahiro; Shibata, Yosei; Wang, Zhiping; Miyadera, Tetsuhiko; Yoshida, Yuji [Chemistry Letters, 2015, vol. 44, # 7, p. 958 - 960]

30
[ 57102-97-3 ]
[ 73183-34-3 ]
[ 1020657-86-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate In 1,4-dioxane at 110℃; for 18h; Inert atmosphere;	2.1.2. Synthesis of 9-ethyl-3-(4,4,5,5-termethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (2) A mixture of 14.2 g of 3-bromo-9-ethyl-9H-carbazole (0.052 mol, 1.0eq), bis(pinacolato)diboron (0.062 mol, 1.2 eq), potassium acetate(0.103 mol, 2.0 eq) and tetrakis(triphenylphosphine) palladium(0)(0.003 mol, 0.05 eq) in 1,4-dioxane (300 mL) was reflux under nitrogenfor 18 h at 110 °C. The reaction mixture was celite filtered, before beingdiluted with ethyl acetate and rinsed with water. The organic layer wasdried in vacuo with anhydrous MgSO4 to yield the crude product. Thecrude product was purified using dichloromethane/n-hexane columnchromatography on silica gel. The product was obtained as whitepowder (10.4 g, 62%).
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium acetate
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane Reflux; Inert atmosphere;	1.1 (1) Synthesis method of ligand The synthesis method of the main ligand: 3-bromocarbazole and bromoethane are dissolved in tetrahydrofuran, heated to reflux under magnetic stirring, cooled to room temperature, extracted with dichloromethane, the organic phase is dehydrated by anhydrous magnesium sulfate, and then reduced. Spin to dry, and silica gel column chromatography obtains 9-ethyl-3-bromocarbazole (compound 1); Phenylphosphino)ferrocene]palladium dichloride was added to the eggplant-shaped flask, deoxygenated, injected with dioxane, heated to reflux under nitrogen protection, cooled to room temperature after the reaction was completed, and extracted with dichloromethane , the organic phase was dewatered by anhydrous magnesium sulfate, then spin-dried under reduced pressure, and silica gel column chromatography was used to obtain compound 2; compound 2, 2-bromopyridine and tetrakis(triphenyl)phosphine palladium were dissolved in toluene, methanol and saturated potassium carbonate In the mixed solution of the solution, under the protection of nitrogen, reflux in an oil bath at 85°C for 18 hours. After the reaction is completed, it is cooled to room temperature naturally and extracted with dichloromethane. Column chromatography gave the target product compound 3 with the following structure.

Reference： [1]Joung, Kuk Soung; Kim, Kyu Sung; Kim, Seung Uk; Tak, So Hyun; Yu, Jae-Woong [Organic electronics, 2022, vol. 100]
[2]Xue, Pengchong; Sun, Jiabao; Chen, Peng; Gong, Peng; Yao, Boqi; Zhang, Zhenqi; Qian, Chong; Lu, Ran [Journal of Materials Chemistry C, 2015, vol. 3, # 16, p. 4086 - 4092]
[3]Current Patent Assignee: NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS - CN113651857, 2021, A Location in patent: Paragraph 0039-0042

31
[ 74-96-4 ]
[ 1592-95-6 ]
[ 57102-97-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium hydroxide In dimethyl sulfoxide at 50℃; for 24h; Inert atmosphere;	3-Bromo-9-ethyl-9H-carbazole: Under nitrogen atmosphere, a mixture of 3-bromo-9H-carbazole (13 g, 40 mmol), bromoethane (5.24 g, 40 mmol), KOH (6.72 g, 120 mmol) and 120 ml dimethylsulphoxide were stirred at 50 °C for 24 h. After cooling, the reaction mixture was quenched by the addition of water and extracted with CH2Cl2, The combined organic layer was washed with dilute HCl and brine several times, dried over anhydrous MgSO4, filtered and evaporated under vacuum. The crude product was purified by recrystallization from ethanol. A white solid was obtained by 16.03 g (Yield: 89%). 1H NMR (400 MHz, CDCl3, ppm) d8.25-8.20 (d,1H), 8.10-8.00 (d, 1H), 7.60-7.45 (m, 2H), 7.43-7.35 (d, 1H), 7.30-7.20 (m, 2H), 4.35-4.25 (m, 2H), 1.50-1.35 (t, 3H).
89%	With potassium hydroxide In dimethyl sulfoxide at 50℃; for 24h; Inert atmosphere;	1 Compound 3-bromo-9-ethyl carbazole he 3-bromo-carbazole (13g, 40mmol), bromoethanesulphonate (5.24g, 40mmol), potassium hydroxide (6.72g, 120mmol) and 120 ml of dimethyl sulfoxide is added to the dual-port flask. Pumping three times, in N2atmosphere, 50 °C stirring under the conditions of 24 hours. Wait for the temperature to drop to room temperature, by adding an appropriate amount of material, a plurality of times and extraction with methylene chloride. The obtained organic solution with hydrochloric acid aqueous solution after washing three times, with anhydrous magnesium sulphate dried organic solution. By rotating the evaporimeter removal of the organic solvent, the obtained solid crude product is recrystallized in ethanol. Finally obtain the white pure product 16.03g (89%).
78%	Stage #1: 3-bromo-9H-carbazole With potassium hydroxide In acetone at 20℃; for 4h; Stage #2: ethyl bromide In acetone at 20℃;	1 Synthesis of Compound 1: Example 1 In a 500mL round bottomed flask, KOH (260mmol, 14.63g) was dissolved in a suitable amount of acetone (200mL) and stirred at room temperature for 30 minutes, and then dissolved in acetone 3-bromo-carbazole (52mmol, 2.80g) was added to the above solution the mixture was stirred at room temperature for 4 hours, and finally dissolved in acetone bromoethane (78mmol, 6mL) was added slowly, stirred overnight at room temperature. after completion of the reaction the solid was filtered off KOH Rotavapor rotary evaporation, an appropriate amount of tar-like liquid two chloride was dissolved, the sample preparation silica gel, by column chromatography using petroleum ether: dichloromethane (PE: DCM, v / v , 50: 1)as eluent, to give purified compound 1, as a white flocculent solid product: 11.12g, yield: 78%.

70%	Stage #1: 3-bromo-9H-carbazole With sodium hydroxide In tetrahydrofuran; water at 20℃; for 1.5h; Stage #2: ethyl bromide In tetrahydrofuran; water at 55℃; for 12h;
	With sodium hydride
	With potassium hydroxide In N,N-dimethyl-formamide at 80℃; for 12h;
	With caesium carbonate In N,N-dimethyl-formamide
	Stage #1: 3-bromo-9H-carbazole With sodium hydroxide In tetrahydrofuran at 20℃; for 1.5h; Stage #2: ethyl bromide In tetrahydrofuran for 12h;	1.1 (1) Synthesis of Compound (3) 2.46 g of 3-bromocarbazole (10 mmol) (1) and 0.8 g of sodium hydroxide (20 mmol) was added to the 20 mL stirring at room temperature in a high pressure tube of tetrahydrofuran. after 1.5 h, 6.56 g of ethyl bromide (60 mmol) was added and the reaction was carried out for about 12 h. After the reaction is completed, the reacted system is distilled under reduced pressure, and the solvent is evaporated to give a crude product, which is purified by column chromatography with ethyl acetate and petroleum ether as a mobile phase at a volume ratio of 1:30. 3-bromo-9-ethylcarbazole (3);
	With sodium hydroxide In tetrahydrofuran at 20℃; for 13.5h;	1.1 (1) Synthesis of Compound (3): 2.46 g of 3-bromocarbazole (10 mmol) (1) and 0.8 g of sodium hydroxide (20 mmol) were added to a high pressure tube containing 20 mL of tetrahydrofuran.After stirring at room temperature, after adding 1.56 g of ethyl bromide (60 mmol) for 1.5 h, the reaction was completed for 12 h. After the reaction was completed, the system after the reaction was distilled under reduced pressure.After spinning the solvent to obtain a crude product,Purification by column chromatography with ethyl acetate and petroleum ether as mobile phase in a volume ratio of 1:30 to obtain 3-bromo-9-ethylcarbazole (3);
	Stage #1: 3-bromo-9H-carbazole With sodium hydroxide In tetrahydrofuran at 55℃; for 1.5h; Stage #2: ethyl bromide In tetrahydrofuran for 12h;	1.1 (1) Will be 2.46 g 3 - bromo carbazole (10 mmol) and 0.8 g sodium hydroxide (20 mmol) added with 20 ml tetrahydrofuran of the high-pressure tube, after stirring, put into the 55 °C oil bath in the pan constant temperature reaction, 1.5 h add 6.56 g bromo ethane (60 mmol), instead on invitation 12 h, after the reaction is finished, the system after the reaction is distilled under reduced pressure, after the turns on lathe does solvent to get the crude product, to the volume ratio of 1:30 of ethyl acetate and petroleum ether as the mobile phase to column chromatography separation purify to get the 3 - bromo -9 - ethane - 9H - carbazole
	In tetrahydrofuran Reflux;	1.1 (1) Synthesis method of ligand The synthesis method of the main ligand: 3-bromocarbazole and bromoethane are dissolved in tetrahydrofuran, heated to reflux under magnetic stirring, cooled to room temperature, extracted with dichloromethane, the organic phase is dehydrated by anhydrous magnesium sulfate, and then reduced. Spin to dry, and silica gel column chromatography obtains 9-ethyl-3-bromocarbazole (compound 1); Phenylphosphino)ferrocene]palladium dichloride was added to the eggplant-shaped flask, deoxygenated, injected with dioxane, heated to reflux under nitrogen protection, cooled to room temperature after the reaction was completed, and extracted with dichloromethane , the organic phase was dewatered by anhydrous magnesium sulfate, then spin-dried under reduced pressure, and silica gel column chromatography was used to obtain compound 2; compound 2, 2-bromopyridine and tetrakis(triphenyl)phosphine palladium were dissolved in toluene, methanol and saturated potassium carbonate In the mixed solution of the solution, under the protection of nitrogen, reflux in an oil bath at 85°C for 18 hours. After the reaction is completed, it is cooled to room temperature naturally and extracted with dichloromethane. Column chromatography gave the target product compound 3 with the following structure.

Reference： [1]Zhang, Qingwei; Fang, Da; Jiang, Hongji; Zhang, Xinwen; Zhang, Hongmei [Organic electronics, 2015, vol. 27, p. 173 - 182]
[2]Current Patent Assignee: NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS - CN105418679, 2016, A Location in patent: Paragraph 0038; 0039; 0040
[3]Current Patent Assignee: ANHUI UNIVERSITY - CN110003173, 2019, A Location in patent: Paragraph 0019; 0034; 0035
[4]Peng, Min; Yin, Junling; Lin, Weiying [New Journal of Chemistry, 2018, vol. 42, # 23, p. 18521 - 18525]
[5]Xue, Pengchong; Sun, Jiabao; Chen, Peng; Gong, Peng; Yao, Boqi; Zhang, Zhenqi; Qian, Chong; Lu, Ran [Journal of Materials Chemistry C, 2015, vol. 3, # 16, p. 4086 - 4092]
[6]Karuppasamy, Ayyanar; Stalindurai, Kesavan; Peng, Jia-De; Ho, Kuo-Chuan; Ramalingan, Chennan [Physical Chemistry Chemical Physics, 2016, vol. 18, # 43, p. 30105 - 30116]
[7]Diaz, Philippe; Horne, Eric; Xu, Cong; Hamel, Ernest; Wagenbach, Michael; Petrov, Ravil R.; Uhlenbruck, Benjamin; Haas, Brian; Hothi, Parvinder; Wordeman, Linda; Gussio, Rick; Stella, Nephi [European Journal of Medicinal Chemistry, 2018, vol. 159, p. 74 - 89]
[8]Current Patent Assignee: UNIVERSITY OF JINAN (SHANDONG) - CN108822019, 2018, A Location in patent: Paragraph 0026
[9]Current Patent Assignee: UNIVERSITY OF JINAN (SHANDONG) - CN108997195, 2018, A Location in patent: Paragraph 0022
[10]Current Patent Assignee: UNIVERSITY OF JINAN (SHANDONG) - CN109369636, 2019, A Location in patent: Paragraph 0023
[11]Current Patent Assignee: NANJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS - CN113651857, 2021, A Location in patent: Paragraph 0039-0042

32
[ 57102-97-3 ]
[ 185990-03-8 ]
[ 1020657-86-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: dimethylphenyl(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)silane With potassium methanolate In 1,2-dimethoxyethane at 30℃; for 0.166667h; Stage #2: 3-bromo-9-ethyl-9H-carbazole In 1,2-dimethoxyethane at 30℃; for 1h;

Reference： [1]Yamamoto, Eiji; Ukigai, Satoshi; Ito, Hajime [Chemical Science, 2015, vol. 6, # 5, p. 2943 - 2951]

33
[ 57102-97-3 ]
[ 54663-78-4 ]
3-(thiophen-2’-yl)-9-ethylcarbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene for 14h; Inert atmosphere; Reflux;	Synthesis of 3-(thiophen-2’-yl)-9 -ethylcarbazole (4) Under a N2 atmosphere, to a mixture of 3-bromo-9-ethylcarbazole 3 (1.38 g, 5.03mmol), thiopehen-2- tributylstannane (2.25 g, 6.03 mmol), and Pd(PPh3)4 ( 290 mg,0.25 mmol) , toluene (15 ml) was added and refluxed for 14h. After cooling to r.t., thesolvent was removed under reduce pressure. The residue was purified by columnchromatography (SiO2, eluent: hexane). Further purification was carried out by HPLC(eluent: hexane:EtOAc =20:1) gave 4 in 64 % yield (896 mg) as a green solid. 1H (400MHz,acetone-d6) : 8.47 (d, 1H, J = 1.24 Hz), 8.24 (dd, 1H, J = 7.71Hz/1.83 Hz),7.80(dd, J= 7.80Hz/1.86 Hz), 7.64-7.58 (d, d, 2H, J = 8.48, 8.29), 7.51-7.47 (ddd, d, 2H, J =7.13 Hz,/2.27 Hz/1.21 Hz, 1.17 Hz),7.40 (dd, 1H, J = 5.15 Hz/ 1.13 Hz) 7.24 (ddd, 1H,J = 7.02Hz/ 1.50 Hz/0.91 Hz), 7.14 (dd, 1H, J = 5.15 Hz/1.50 Hz), 4.51 (qult, 2H), 1.43(t, 3H). 13C (100 MHz, acetone-d6): 146.47, 141.48, 140.49, 129.02, 127.00, 126.59, 124.98, 124.58, 124.29, 123.73, 122.99, 121.43, 119.96, 118.38, 110.19, 109.95, 38.17,14.13. HRMS-EI (m/z): calcd for C18H15NS, 277.0925; found, 277.0922.

Reference： [1]Kono, Takahiro; Shibata, Yosei; Wang, Zhiping; Miyadera, Tetsuhiko; Yoshida, Yuji [Chemistry Letters, 2015, vol. 44, # 7, p. 958 - 960]

34
[ 57102-97-3 ]
C₃₄H₄₈S₃ [ No CAS ]
C₄₈H₅₉NS₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: C₃₄H₄₈S₃ With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex In tetrahydrofuran at 20℃; for 3h; Schlenk technique; Inert atmosphere; Stage #2: 3-bromo-9-ethyl-9H-carbazole With Pd-PEPPSI-IPr In tetrahydrofuran at 60℃; for 24h; Schlenk technique; Inert atmosphere;