Name: 211737-28-9|2-Bromo-5-hexylthiophene|98%
Brand: Ambeed
SKU: A847688
Price: 6.0 USD
Availability: InStock
Rating: 98 (30 reviews)

1
[ 18794-77-9 ]
[ 211737-28-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 12.1667h;	In a 300mL three-neck flask having a dropping funnel, <strong>[18794-77-9]<strong>[18794-77-9]2-hexylthiophen</strong>e</strong> (compound indicated by "1") (6.2g, 37mmol) was dissolved in DMF (150mL). Then, a solution obtained by dissolving NBS (6.56g, 37mmol) in DMF (15mL) was added thereto in drops at a room temperature over 10 minutes and thereafter stirred for 12 hours at a room temperature. To the reaction solution thus obtained, a saturated sodium hydrogen carbonate solution (150mL) was added and then stirred for 30 minutes. Then, hexane (80mL) was added thereto. Subsequently, a water layer was separated and then extracted with hexane (80mL×2). Then, organic layers were collected, washed with water (100mLx3), and dried with anhydrous magnesium sulfate. After the resulting solution was filtered, a solvent was removed therefrom under a reduced pressure. As a result, a compound indicated by "2" was obtained in the form of yellow liquid (8.9g, 98%). TLC Rf=0.79 (silica gel, methylene chloride: hexane = 1:1); 1H-NMR (400MHz, CDCl3, TMS) 6.84 (1H, d, J=3.6Hz, position 3), 6.53 (1H, dt, J=3.6 and 1.2Hz, position 4), 2.74 (2H, t, J=7.6Hz), 1.62 (2H, m), 1.33 (6H, m), 0.88 (3H, t, J=7.2Hz); MS (70eV, EI) m/z=248 (M+).
92%	With N-Bromosuccinimide; In chloroform; N,N-dimethyl-formamide; at 0 - 20℃; for 24h;	A solution of <strong>[18794-77-9]<strong>[18794-77-9]2-hexylthiophen</strong>e</strong> (6.72 g, 40 mmol) in CHCl3 (100 mL) was placed in a 250 mL three-necked flask at 0 C, and then DMF (40 mL) with NBS (7.12 g, 40 mmol) mixture was added dropwisely. The reaction mixture was warmed up to room temperature and stirred for overnight absent from light, after this the mixture was poured into water, extracted by CH2Cl2, organic phase was washed several times with sodium hydrogen carbonate aqueous solution, and dried by a rotary evaporator to give a crude product. Further purification was carried out by column chromatography on the silica gel using petroleum ether as the eluent to obtain a colorless liquid (9.1 g, yield 92 %). 1H NMR (500 MHz, CDCl3) delta 6.84 (d, J = 3.6 Hz, 1 H), 6.53 (d, J = 3.5 Hz, 1 H), 2.74 (t, J = 7.6 Hz, 2 H), 1.68-1.58 (m, 2 H), 1.42-1.22 (m, 6 H), 0.99-0.82 (m, 3H). MS (m/z) for C10H15BrS: calcd. 246.01; found, 246.01 (M+). Elemental Anal. calcd for C10H15BrS (%): C, 48.59; H, 6.12; Br, 32.32; S, 12.97. Found (%): C, 48.62; H, 6.13; S, 13.01.
90%	With N-Bromosuccinimide; In chloroform; acetic acid; at 20℃; for 2h;	Compound 2a (30 g, 178 mmol) was dissolved in chloroform/acetic acid (100 mL/100 mL, v/v) and added NBS (34.9 g, 198 mmol) at room temperature. The reaction mixture was stirred for 2 h and quenched with water (100 mL). The product was extracted with CH2Cl2 and washed with water, brine, and dried over MgSO4, and then evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel with hexane as eluent to give 3a as colorless liquid. Yield: 39 g (90%); IR (KBr): 3068 cm-1 (sp2 C-H), 2951-2852 cm-1 (sp3 C-H), 1521-1436 cm-1 (C=C); 1H NMR (300 MHz, CDCl3, ppm): delta 6.86-6.85 (d, 1H, J=3.6 Hz), 6.55-6.54 (d, 1H, J=3.6 Hz), 2.78-2.73 (t, 2H, J=7.2 Hz), 1.67-1.62 (m, 2H), 1.35-1.32 (m, 6H), 1.12-0.91 (t, 3H, J=1.8 Hz); 13C NMR (75 MHz, CDCl3, ppm): delta 147.66, 129.37, 124.33, 108.55, 31.53, 31.43, 30.34, 28.66, 22.57, 14.08 Hz; EIMS m/z (%): 246 (100, M+).

Reference： [1]Organic Letters,2011,vol. 13,p. 5208 - 5211
[2]Organic Letters,2014,vol. 16,p. 2330 - 2333
[3]Patent: EP2138545,2009,A1 .Location in patent: Page/Page column 17-18; 33
[4]Journal of Materials Chemistry C,2013,vol. 1,p. 3467 - 3481
[5]Chemistry - An Asian Journal,2012,vol. 7,p. 225 - 232
[6]Dyes and Pigments,2015,vol. 113,p. 458 - 464
[7]Journal of the American Chemical Society,2006,vol. 128,p. 2336 - 2345
[8]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 3810 - 3816
[9]Tetrahedron,2013,vol. 69,p. 8191 - 8198
[10]Macromolecules,2014,vol. 47,p. 1008 - 1020
[11]Journal of Organic Chemistry,1998,vol. 63,p. 5497 - 5506
[12]Organic Letters,2013,vol. 15,p. 1202 - 1205
[13]Organic Letters,2002,vol. 4,p. 2067 - 2070
[14]Organic Letters,2004,vol. 6,p. 273 - 276
[15]Journal of the American Chemical Society,2005,vol. 127,p. 2406 - 2407
[16]Tetrahedron Letters,2007,vol. 48,p. 779 - 784
[17]Organic Letters,2018,vol. 20,p. 7270 - 7273
[18]Tetrahedron,2010,vol. 66,p. 8778 - 8784
[19]Journal of Materials Chemistry,2002,vol. 12,p. 2706 - 2721
[20]Molecular Crystals and Liquid Crystals,2004,vol. 410,p. 1/[529]-12/[540]
[21]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2001,vol. 364,p. 881 - 888
[22]Angewandte Chemie - International Edition,2011,vol. 50,p. 10682 - 10685
[23]Chinese Journal of Chemistry,2012,vol. 30,p. 577 - 584
[24]Journal of Physical Chemistry A,2012,vol. 116,p. 7927 - 7936
[25]Science China Chemistry,2013,vol. 56,p. 997 - 1003
[26]Chemistry - An Asian Journal,2016,vol. 11,p. 2932 - 2937
[27]CrystEngComm,2018,vol. 20,p. 1669 - 1678
[28]Dyes and Pigments,2018,vol. 157,p. 179 - 189

2
[ 492-97-7 ]
[ 211737-28-9 ]
[ 151271-42-0 ]

Reference： [1]Chemistry - An Asian Journal,2012,vol. 7,p. 225 - 232
[2]Journal of Organic Chemistry,1998,vol. 63,p. 5497 - 5506

3
[ 211737-28-9 ]
[ 211737-29-0 ]

Yield	Reaction Conditions	Operation in experiment
37%	With 3-chloro-benzenecarboperoxoic acid In dichloromethane Ambient temperature;

Reference： [1]Barbarella; Favaretto; Sotgiu; Zambianchi; Antolini; Pudova; Bongini [Journal of Organic Chemistry, 1998, vol. 63, # 16, p. 5497 - 5506]

4
[ 3140-93-0 ]
[ 211737-28-9 ]
[ 442911-11-7 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: 2-bromo-5-hexylthiophene With magnesium In diethyl ether Stage #2: 2,3-dibromothiophen With [1,3-bis(diphenylphosphino)propane]nickel(II) dichloride In diethyl ether at 20℃; for 20h; Further stages.;
87%	With magnesium In diethyl ether at 0℃; for 20h;
	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); iodine; magnesium In diethyl ether for 24h; Inert atmosphere; Reflux;

Stage #1: 2-bromo-5-hexylthiophene With magnesium In diethyl ether at 0℃; Stage #2: 2,3-dibromothiophen

Reference： [1]Xia, Chuanjun; Fan, Xiaowu; Locklin, Jason; Advincula, Rigoberto C. [Organic Letters, 2002, vol. 4, # 12, p. 2067 - 2070]
[2]Advincula, Rigoberto C. [Dalton Transactions, 2006, # 23, p. 2778 - 2784]
[3]Gao, Lei; Zhang, Jing; He, Chang; Shen, Suling; Zhang, Yi; Liu, Hongtao; Sun, Qingjiang; Li, Yongfang [Science China Chemistry, 2013, vol. 56, # 7, p. 997 - 1003]
[4]Lin, Chien-Min; Li, Ming-Shiou; Dwivedi, Atul Kumar; Lin, Hong-Cheu [Dyes and Pigments, 2018, vol. 157, p. 179 - 189]

5
[ 5720-07-0 ]
[ 211737-28-9 ]
2-(4-methoxyphenyl)-5-hexylthiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate In 1,2-dimethoxyethane; water
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate In 1,2-dimethoxyethane; water for 6h; Reflux;

Reference： [1]Campbell, Neil L.; Duffy, Warren L.; Thomas, Gareth I.; Wild, Janine H.; Kelly, Stephen M.; Bartle, Kevin; O'Neill, Mary; Minter, Vicky; Tuffin, Rachel P. [Journal of Materials Chemistry, 2002, vol. 12, # 9, p. 2706 - 2721]
[2]Bartle, Kevin; Campbell, Neil; Duffy, Warren L.; Kelly, Stephen M.; Minter, Vicki; O'Neill, Mary; Tuffin, Rachel P. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 881 - 888]
[3]Location in patent: scheme or table Jing, Shan; Zhang, Ruilin; Dai, Heng; Du, Chao; Cheng, Xiaohong [Chinese Journal of Chemistry, 2012, vol. 30, # 3, p. 577 - 584]

6
[ 55164-48-2 ]
[ 211737-28-9 ]
2-[5'-hexyl-5-(2,2'-dithienyl)]benzo[b]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%	Stage #1: 2-(thiophene-2-yl)benzo[b]thiophene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Stage #2: With tributyltin chloride In tetrahydrofuran; hexane at 20℃; for 2h; Stage #3: 2-bromo-5-hexylthiophene In toluene for 16h; Heating;

Reference： [1]Nicolas, Yohann; Blanchard, Philippe; Levillain, Eric; Allain, Magali; Mercier, Nicolas; Roncali, Jean [Organic Letters, 2004, vol. 6, # 2, p. 273 - 276]

7
[ 29150-63-8 ]
[ 211737-28-9 ]
2,5,8-tris(5-hexyl-2-thienyl)benzo[1,2-b:3,4-b':5,6-b'']trithiophene [ No CAS ]

Reference： [1]Organic Letters,2004,vol. 6,p. 273 - 276

8
[ 98437-23-1 ]
[ 211737-28-9 ]
2-(5-hexyl-2-thienyl)benzo[b]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With barium dihydroxide In 1,2-dimethoxyethane for 20h; Heating;

Reference： [1]Nicolas, Yohann; Blanchard, Philippe; Levillain, Eric; Allain, Magali; Mercier, Nicolas; Roncali, Jean [Organic Letters, 2004, vol. 6, # 2, p. 273 - 276]

9
[ 1003-09-4 ]
[ 211737-28-9 ]
[ 173448-31-2 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: 2-bromothiophene With magnesium In diethyl ether for 4h; Inert atmosphere; Reflux; Stage #2: 2-bromo-5-hexylthiophene With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether for 48h; Inert atmosphere; Reflux;
	With magnesium In diethyl ether Heating;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; magnesium In diethyl ether at 20℃;

Reference： [1]Matsumoto, Kouzou; Kugo, Sota; Takajo, Daisuke; Inaba, Akira; Hirao, Yasukazu; Kurata, Hiroyuki; Kawase, Takeshi; Kubo, Takashi [Chemistry - An Asian Journal, 2012, vol. 7, # 1, p. 225 - 232]
[2]Funahashi, Masahiro; Hanna, Jun-Ichi [Molecular Crystals and Liquid Crystals, 2004, vol. 410, p. 1/[529]-12/[540]]
[3]Location in patent: scheme or table Kirkus, Mindaugas; Wang, Linjun; Mothy, Sebastien; Beljonne, David; Cornil, Jerome; Janssen, Rene A. J.; Meskers, Stefan C. J. [Journal of Physical Chemistry A, 2012, vol. 116, # 30, p. 7927 - 7936]

10
[ 211737-28-9 ]
[ 849138-20-1 ]
2-[6-(5-hexyl-thiophen-2-yl)-anthracen-2-yl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane [ No CAS ]
bis-(5'-hexylthiophen-2'-yl)-2,6-anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; Aliquat 336; sodium carbonate In toluene at 90℃; for 72h;

Reference： [1]Meng, Hong; Sun, Fangping; Goldfinger, Marc B.; Jaycox, Gary D.; Li, Zhigang; Marshall, Will J.; Blackman, Gregory S. [Journal of the American Chemical Society, 2005, vol. 127, # 8, p. 2406 - 2407]

11
[ 162717-58-0 ]
[ 211737-28-9 ]
[ 151271-42-0 ]

Reference： [1]Macromolecules,2004,vol. 37,p. 5692 - 5702

12
[ 5713-61-1 ]
[ 211737-28-9 ]
[ 173448-31-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether Heating;

Reference： [1]Funahashi, Masahiro; Hanna, Jun-Ichi [Molecular Crystals and Liquid Crystals, 2005, vol. 436, p. 225/[1179]-235/[1189]]

13
[ 126213-50-1 ]
[ 211737-28-9 ]
[ 862681-08-1 ]

Yield	Reaction Conditions	Operation in experiment
550 mg	Stage #1: 3,4-(ethylenedioxy)thiophene With n-butyllithium In tetrahydrofuran; hexane Stage #2: With tributyltin chloride In tetrahydrofuran; hexane Stage #3: 2-bromo-5-hexylthiophene In toluene Heating;

Reference： [1]Turbiez, Mathieu; Frre, Pierre; Allain, Magali; Videlot, Christine; Ackermann, Joerg; Roncali, Jean [Chemistry - A European Journal, 2005, vol. 11, # 12, p. 3742 - 3752]

14
[ 195602-17-6 ]
[ 211737-28-9 ]
3',4',3'',4''-bis(ethylenedioxy)-5,5'''-dihexyl-2,2':5',2'':5'',2'''-quaterthiophene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 3742 - 3752

15
[ 211737-28-9 ]
[ 199168-63-3 ]
[ 862681-13-8 ]

Yield	Reaction Conditions	Operation in experiment
2.8 g	Stage #1: 2-(2-thienyl)-(3,4-ethylenedioxythiophene) With n-butyllithium In tetrahydrofuran; hexane for 1h; Stage #2: With tributyltin chloride In tetrahydrofuran; hexane for 0.5h; Stage #3: 2-bromo-5-hexylthiophene In toluene for 12h; Heating;

Reference： [1]Turbiez, Mathieu; Frre, Pierre; Allain, Magali; Videlot, Christine; Ackermann, Joerg; Roncali, Jean [Chemistry - A European Journal, 2005, vol. 11, # 12, p. 3742 - 3752]

16
[ 211737-28-9 ]
[ 1066-54-2 ]
[ 880491-25-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N-ethyl-N,N-diisopropylamine at 85℃; for 18h;
58%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine at 90℃; for 12h; Inert atmosphere;	2.5 4.2.5 [(5-Hexylthiophen-2-yl)ethynyl]trimethylsilane (4a) To a deaerated solution of 3a (34.6 g, 140 mmol) in i-Pr2NH (300 mL) were added Pd(pph3)2Cl2 (2.25 g, 0.28 mmol) and CuI (1.6 g, 8.4 mmol) at room temperature. And then ethynyltrimethylsilane (19.4 mL, 140 mmol) was added dropwise to the reaction mixture and stirred at 90 °C for 12 h, and then allowed to reach at room temperature. The reaction mixture was filtered and solvent was removed by evaporation under reduced pressure and the residue performed flash column chromatography on silica gel with hexane as eluent to give 4a as light brown liquid. Yield: 21.0 g (58%); IR (KBr): 2958-2927 cm-1 (sp2 C-H), 2853 cm-1 (sp3 C-H), 2098 cm-1 (C≡C), 1504-1465 cm-1 (C=C); 1H NMR (300 MHz, CDCl3, ppm): δ 7.01-6.99 (d, 1H, J=3.3 Hz), 6.64-6.62 (d, 1H, J=3.6 Hz), 2.77-2.72 (t, 2H, J=7.2 Hz), 1.67-1.62 (m, 2H), 1.34-1.31 (m, 6H), 1.13-0.92 (t, 3H, J=1.8 Hz); 13C NMR (75 MHz, CDCl3, ppm): δ 147.94, 131.94, 123.95, 119.93, 96.77, 75.98, 65.71, 31.95, 31.57, 31.36, 29.67, 29.39, 22.72, 14.15 Hz; EIMS m/z (%): 264 (100, M+).
39%	With copper(l) iodide; bis(benzonitrile)palladium(II) dichloride; tri-tert-butyl phosphine; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine

Reference： [1]Van Breemen, Albert J. J. M.; Herwig, Peter T.; Chlon, Ceciel H. T.; Sweelssen, Joergen; Schoo, Herman F. M.; Setayesh, Sepas; Hardeman, Willie M.; Martin, Christian A.; De Leeuw, Dago M.; Valeton, Josue J. P.; Bastiaansen, Cees W. M.; Broer, Dirk J.; Popa-Merticaru, Andreea R.; Meskers, Stefan C. J. [Journal of the American Chemical Society, 2006, vol. 128, # 7, p. 2336 - 2345]
[2]Shaik, Baji; Park, Ji Hee; An, Tae Kyu; Noh, Young Ri; Yoon, Soon Byung; Park, Chan Eon; Yoon, Young Jin; Kim, Yun-Hi; Lee, Sang-Gyeong [Tetrahedron, 2013, vol. 69, # 38, p. 8191 - 8198]
[3]Location in patent: experimental part Rondeau-Gagné, Simon; Curutchet, Carles; Grenier, François; Scholes, Gregory D.; Morin, Jean-François [Tetrahedron, 2010, vol. 66, # 23, p. 4230 - 4242]
[4]Ashizawa, Minora; Kato, Reizo; Takanishi, Yoichi; Takezoe, Hideo [Chemistry Letters, 2007, vol. 36, # 6, p. 708 - 709]

17
[ 211737-28-9 ]
[ 147437-99-8 ]
[ 925899-22-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 2-bromo-5-hexylthiophene With iodine; magnesium In tetrahydrofuran Heating; Stage #2: 3-(thiophen-2-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 20℃; Stage #3: With Lawessons reagent In dichloromethane at 20℃;
58%	Stage #1: 2-bromo-5-hexylthiophene With iodine; magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: 3-(thiophen-2-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 20℃; for 6h; Stage #3: With Lawessons reagent In dichloromethane at 20℃; for 6h;

Reference： [1]Mohanakrishnan, Arasambattu K.; Amaladass; Arul Clement [Tetrahedron Letters, 2007, vol. 48, # 5, p. 779 - 784]
[2]Location in patent: experimental part Amaladass, Pitchamuthu; Clement, J. Arul; Mohanakrishnan, Arasambattu K. [European Journal of Organic Chemistry, 2008, # 22, p. 3798 - 3810]

18
[ 211737-28-9 ]
[ 205643-78-3 ]
1-(5-hexylthiophen-2-yl)-3-[5-(thiophen-2-yl)thiophen-2-yl]benzo[c]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	Stage #1: 2-bromo-5-hexylthiophene With iodine; magnesium In tetrahydrofuran Heating; Stage #2: 3-(2,2’-bithiophen-5-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 20℃; Stage #3: With Lawessons reagent In dichloromethane at 20℃;
55%	Stage #1: 2-bromo-5-hexylthiophene With iodine; magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: 3-(2,2’-bithiophen-5-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 20℃; for 6h; Stage #3: With Lawessons reagent In dichloromethane at 20℃; for 6h;

Reference： [1]Mohanakrishnan, Arasambattu K.; Amaladass; Arul Clement [Tetrahedron Letters, 2007, vol. 48, # 5, p. 779 - 784]
[2]Location in patent: experimental part Amaladass, Pitchamuthu; Clement, J. Arul; Mohanakrishnan, Arasambattu K. [European Journal of Organic Chemistry, 2008, # 22, p. 3798 - 3810]

19
[ 211737-28-9 ]
[ 4281-21-4 ]
3,3'-bis(5-hexylthiophen-2-yl)-1,1'-bibenzo[c]thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-bromo-5-hexylthiophene With iodine; magnesium In tetrahydrofuran Heating; Stage #2: 3-(3-phthalidyl)phthalide In tetrahydrofuran at 20℃; Stage #3: With Lawessons reagent In dichloromethane at 20℃;
51%	Stage #1: 2-bromo-5-hexylthiophene With iodine; magnesium In tetrahydrofuran for 2h; Inert atmosphere; Reflux; Stage #2: 3-(3-phthalidyl)phthalide In tetrahydrofuran at 20℃; Stage #3: With Lawessons reagent In dichloromethane at 20℃; for 6h;

Reference： [1]Mohanakrishnan, Arasambattu K.; Amaladass; Arul Clement [Tetrahedron Letters, 2007, vol. 48, # 5, p. 779 - 784]
[2]Location in patent: experimental part Amaladass, Pitchamuthu; Clement, J. Arul; Mohanakrishnan, Arasambattu K. [European Journal of Organic Chemistry, 2008, # 22, p. 3798 - 3810]

20
[ 61676-62-8 ]
[ 211737-28-9 ]
[ 917985-54-7 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 2-bromo-5-hexylthiophene With n-butyllithium In tetrahydrofuran at -70℃; for 0.75h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 25℃; for 18h;
100%	Stage #1: 2-bromo-5-hexylthiophene With n-butyllithium In tetrahydrofuran at -70℃; for 0.75h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at 25℃; for 18h;	2 A degassed THF solution ( 25 mL) containing 2-bromo-5-hexylthiophene (4280 mg, 7.32 mmol) was cooled to -70° C at which point n-butyllithium (8.31 mL, 20.8 mmol) was added dropwise while maintaining the temperature at -70 °C. After the reaction was stirred at this temperature for 45 min, 2-isopropoxy-4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolane (5.30 mL, 26.0 mmol) was added. The reaction was brought to 25 °C and then stirred for 18 h. The addition of methanol (15 mL) turned the reaction opaque white before returning to a clear, colourless solution. The reaction was filtered and solvent removed in vacuo. The crude product was purified using a Si02 plug (hexanes/Ch^C ; 3:1 ; v.v) to produce a yellow oil in quantitative yield. H NMR(CDCI3): δ 7.49 (d, 1 H, 3J = 3.4 Hz, Hb), 6.87 (d, 1 H, 3 = 3.4 Hz, Ha), 2.87 (t, 2H, Hc), 1.70 (quintet, 2H, Hd), 1.34 (m, 18H, He,f,g,i), 0.90 (m, 3 H, Hh). 3C NMR (CDCI3): δ 153.8, 137.5, 125.9, 83.9, 82.9, 31.8, 31.7, 30.3, 28.9, 24.8, 22.7, 14.2.
81.7%	Stage #1: 2-bromo-5-hexylthiophene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 2h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran at -78 - 20℃; Further stages.;

With n-butyllithium In tetrahydrofuran at -78℃;

Reference： [1]Bomben, Paolo G.; Gordon, Terry J.; Schott, Eduardo; Berlinguette, Curtis P. [Angewandte Chemie - International Edition, 2011, vol. 50, # 45, p. 10682 - 10685]
[2]Current Patent Assignee: UNIVERSITY OF CALGARY - WO2012/155247, 2012, A1 Location in patent: Page/Page column 76
[3]Park, Jong-Hwa; Chung, Dae Sung; Park, Jong-Won; Ahn, Taek; Kong, Hoyoul; Jung, Young Kwan; Lee, Jonghee; Yi, Mi Hye; Park, Chan Eon; Kwon, Soon-Ki; Shim, Hong-Ku [Organic Letters, 2007, vol. 9, # 13, p. 2573 - 2576]
[4]Zhu, Linna; Wang, Rui; Tan, Luxi; Liang, Xianfeng; Zhong, Cheng; Wu, Fei [Chemistry - An Asian Journal, 2016, vol. 11, # 20, p. 2932 - 2937]

21
[ 211737-28-9 ]
[ 710338-92-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Pd(PPh₃)4; CuI; DIPA 2: KOH
	Multi-step reaction with 2 steps 1: 80 percent / Pd(PPh₃)4; diisopropylethylamine; CuI / 18 h / 85 °C 2: TBAF supported on silica / tetrahydrofuran / 0.08 h
	Multi-step reaction with 2 steps 1: diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / 12 h / 90 °C / Inert atmosphere 2: tetrabutyl ammonium fluoride / tetrahydrofuran; hexane / 12 h / 20 °C

Reference： [1]Ashizawa, Minora; Kato, Reizo; Takanishi, Yoichi; Takezoe, Hideo [Chemistry Letters, 2007, vol. 36, # 6, p. 708 - 709]
[2]Van Breemen, Albert J. J. M.; Herwig, Peter T.; Chlon, Ceciel H. T.; Sweelssen, Joergen; Schoo, Herman F. M.; Setayesh, Sepas; Hardeman, Willie M.; Martin, Christian A.; De Leeuw, Dago M.; Valeton, Josue J. P.; Bastiaansen, Cees W. M.; Broer, Dirk J.; Popa-Merticaru, Andreea R.; Meskers, Stefan C. J. [Journal of the American Chemical Society, 2006, vol. 128, # 7, p. 2336 - 2345]
[3]Shaik, Baji; Park, Ji Hee; An, Tae Kyu; Noh, Young Ri; Yoon, Soon Byung; Park, Chan Eon; Yoon, Young Jin; Kim, Yun-Hi; Lee, Sang-Gyeong [Tetrahedron, 2013, vol. 69, # 38, p. 8191 - 8198]

22
[ 211737-28-9 ]
2,6-bis(5-hexylthiophen-2-yl)-9,10-bis[(triisopropylsilanyl)ethynyl]anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tert-butyllithium / tetrahydrofuran; pentane / 2 h / -78 °C 1.2: 81.7 percent / tetrahydrofuran / -78 - 20 °C 2.1: 67.2 percent / sodium carbonate; Aliquat(R) 336 / tetrakis(triphenylphosphine)palladium⁽⁰⁾ / toluene / 72 h / 90 °C

Reference： [1]Park, Jong-Hwa; Chung, Dae Sung; Park, Jong-Won; Ahn, Taek; Kong, Hoyoul; Jung, Young Kwan; Lee, Jonghee; Yi, Mi Hye; Park, Chan Eon; Kwon, Soon-Ki; Shim, Hong-Ku [Organic Letters, 2007, vol. 9, # 13, p. 2573 - 2576]

23
[ 111-25-1 ]
[ 211737-28-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: n-BuLi / -78 °C 2: 62 percent / NBS / dimethylformamide / 40 h
	Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C 1.2: 75 percent / tetrahydrofuran; hexane / -40 - 20 °C 2.1: 90 percent / NBS / tetrahydrofuran / 0 - 20 °C

Reference： [1]Mohanakrishnan, Arasambattu K.; Amaladass; Arul Clement [Tetrahedron Letters, 2007, vol. 48, # 5, p. 779 - 784]
[2]Van Breemen, Albert J. J. M.; Herwig, Peter T.; Chlon, Ceciel H. T.; Sweelssen, Joergen; Schoo, Herman F. M.; Setayesh, Sepas; Hardeman, Willie M.; Martin, Christian A.; De Leeuw, Dago M.; Valeton, Josue J. P.; Bastiaansen, Cees W. M.; Broer, Dirk J.; Popa-Merticaru, Andreea R.; Meskers, Stefan C. J. [Journal of the American Chemical Society, 2006, vol. 128, # 7, p. 2336 - 2345]

24
[ 211737-28-9 ]
5,5''-bis(5-hexyl-2-thienylethynyl)-[2,2':5',2'']-terthiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 80 percent / Pd(PPh₃)4; diisopropylethylamine; CuI / 18 h / 85 °C 2: TBAF supported on silica / tetrahydrofuran / 0.08 h 3: 3.8 g / Pd(PPh₃)4; diisopropylethylamine; CuI / 85 °C / Heating

Reference： [1]Van Breemen, Albert J. J. M.; Herwig, Peter T.; Chlon, Ceciel H. T.; Sweelssen, Joergen; Schoo, Herman F. M.; Setayesh, Sepas; Hardeman, Willie M.; Martin, Christian A.; De Leeuw, Dago M.; Valeton, Josue J. P.; Bastiaansen, Cees W. M.; Broer, Dirk J.; Popa-Merticaru, Andreea R.; Meskers, Stefan C. J. [Journal of the American Chemical Society, 2006, vol. 128, # 7, p. 2336 - 2345]

25
[ 211737-28-9 ]
4-(5-hexyl-thiophen-2-yl)-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O 2: boron tribromide / CH₂Cl₂ 3: H₃O⁽¹⁺⁾
	Multi-step reaction with 2 steps 1: BBr₃
	Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / 1,2-dimethoxyethane; water / 6 h / Reflux 2: boron tribromide / dichloromethane / 24 h / -78 - 20 °C

Reference： [1]Bartle, Kevin; Campbell, Neil; Duffy, Warren L.; Kelly, Stephen M.; Minter, Vicki; O'Neill, Mary; Tuffin, Rachel P. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 881 - 888]
[2]Campbell, Neil L.; Duffy, Warren L.; Thomas, Gareth I.; Wild, Janine H.; Kelly, Stephen M.; Bartle, Kevin; O'Neill, Mary; Minter, Vicky; Tuffin, Rachel P. [Journal of Materials Chemistry, 2002, vol. 12, # 9, p. 2706 - 2721]
[3]Jing, Shan; Zhang, Ruilin; Dai, Heng; Du, Chao; Cheng, Xiaohong [Chinese Journal of Chemistry, 2012, vol. 30, # 3, p. 577 - 584]

26
[ 211737-28-9 ]
(2E,4E)-Hexa-2,4-dienoic acid 4-(5-hexyl-thiophen-2-yl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O 2: boron tribromide / CH₂Cl₂ 3: H₃O⁽¹⁺⁾ 4: DCC; DMAP / CH₂Cl₂
	Multi-step reaction with 3 steps 1: BBr₃ 2: DCC; DMAP

Reference： [1]Bartle, Kevin; Campbell, Neil; Duffy, Warren L.; Kelly, Stephen M.; Minter, Vicki; O'Neill, Mary; Tuffin, Rachel P. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 881 - 888]
[2]Campbell, Neil L.; Duffy, Warren L.; Thomas, Gareth I.; Wild, Janine H.; Kelly, Stephen M.; Bartle, Kevin; O'Neill, Mary; Minter, Vicky; Tuffin, Rachel P. [Journal of Materials Chemistry, 2002, vol. 12, # 9, p. 2706 - 2721]

27
[ 211737-28-9 ]
(E)-Hex-2-enoic acid 4-(5-hexyl-thiophen-2-yl)-phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O 2: boron tribromide / CH₂Cl₂ 3: H₃O⁽¹⁺⁾ 4: DCC; DMAP / CH₂Cl₂
	Multi-step reaction with 3 steps 1: BBr₃ 2: DCC; DMAP

Reference： [1]Bartle, Kevin; Campbell, Neil; Duffy, Warren L.; Kelly, Stephen M.; Minter, Vicki; O'Neill, Mary; Tuffin, Rachel P. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2001, vol. 364, p. 881 - 888]
[2]Campbell, Neil L.; Duffy, Warren L.; Thomas, Gareth I.; Wild, Janine H.; Kelly, Stephen M.; Bartle, Kevin; O'Neill, Mary; Minter, Vicky; Tuffin, Rachel P. [Journal of Materials Chemistry, 2002, vol. 12, # 9, p. 2706 - 2721]

28
[ 211737-28-9 ]
[ 442911-53-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 87 percent / Mg / NidpppCl₂ / diethyl ether / 20 h / 0 °C 2.1: BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C 2.2: tributyltin chloride / tetrahydrofuran; hexane / 3 h / -78 - 20 °C 2.3: 1.31 g / Pd(PPh₃)4 / dimethylformamide / 24 h / 100 °C
	Multi-step reaction with 3 steps 1.1: magnesium / diethyl ether / 0 °C 1.2: NiddpCl₂ 2.1: n-butyllithium / tetrahydrofuran; hexane / 5 h / -78 °C / Inert atmosphere 3.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 24 h / 100 °C / Inert atmosphere

Reference： [1]Advincula, Rigoberto C. [Dalton Transactions, 2006, # 23, p. 2778 - 2784]
[2]Lin, Chien-Min; Li, Ming-Shiou; Dwivedi, Atul Kumar; Lin, Hong-Cheu [Dyes and Pigments, 2018, vol. 157, p. 179 - 189]

29
[ 211737-28-9 ]
[ 151271-42-0 ]

Reference： [1]Molecular Crystals and Liquid Crystals,2005,vol. 436,p. 225/[1179]-235/[1189]
[2]Molecular Crystals and Liquid Crystals,2004,vol. 410,p. 1/[529]-12/[540]

30
[ 211737-28-9 ]
[ 655249-04-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 75 percent / Ni(dppp)Cl₂ / diethyl ether / Heating 2: 80 percent / NBS / tetrahydrofuran
	Multi-step reaction with 2 steps 1: Mg / Ni(dppp)Cl₂ / diethyl ether / Heating 2: NBS / tetrahydrofuran / 20 °C

Reference： [1]Funahashi, Masahiro; Hanna, Jun-Ichi [Molecular Crystals and Liquid Crystals, 2005, vol. 436, p. 225/[1179]-235/[1189]]
[2]Funahashi, Masahiro; Hanna, Jun-Ichi [Molecular Crystals and Liquid Crystals, 2004, vol. 410, p. 1/[529]-12/[540]]

31
[ 211737-28-9 ]
[ 524937-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Pd(AsPh₃)4 / toluene 2: 75 percent / NBS; acetic acid / CH₂Cl₂ / 0.25 h
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 2.17 h / -90 - -20 °C / Inert atmosphere 1.2: -70 - 20 °C / Inert atmosphere 1.3: Reflux; Inert atmosphere 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C / Darkness

Reference： [1]Melucci, Manuela; Barbarella, Giovanna; Zambianch, Massimo; Benzi, Mario; Biscarini, Fabio; Cavallini, Massimiliano; Bongini, Alessandro; Fabbroni, Serena; Mazzeo, Marco; Anni, Marco; Gigli, Giuseppe [Macromolecules, 2004, vol. 37, # 15, p. 5692 - 5702]
[2]Matsumoto, Kouzou; Kugo, Sota; Takajo, Daisuke; Inaba, Akira; Hirao, Yasukazu; Kurata, Hiroyuki; Kawase, Takeshi; Kubo, Takashi [Chemistry - An Asian Journal, 2012, vol. 7, # 1, p. 225 - 232]

32
[ 111-25-1 ]
[ 211737-28-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: n-butyl lithium / tetrahydrofuran / 0.75 h / -78 °C 1.2: 96 percent / tetrahydrofuran / 3 h / 20 °C 2.1: 80 percent / NBS / dimethylformamide / 10 h / 20 °C
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -60 - 0 °C / Inert atmosphere 1.2: -60 - 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 20 °C / Darkness
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / 24 h / -60 - 20 °C 2: N-Bromosuccinimide / tetrahydrofuran / 1 h / 0 - 5 °C

	Multi-step reaction with 2 steps 1.1: n-butyllithium / 0.5 h / -78 °C 1.2: 48 h / Reflux 2.1: N-Bromosuccinimide / chloroform; acetic acid / 20 °C
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 12 h / -78 - 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide; acetic acid / chloroform / 2 h / 20 °C
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 12 h / -78 - 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 2: N-Bromosuccinimide / chloroform / 20 °C
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 12 h / -78 - 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide / chloroform; acetic acid / 2 h / 20 °C
	Multi-step reaction with 2 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / 0 °C 1.2: 0 - 20 °C 2.1: N-Bromosuccinimide; acetic acid / 2 h
	Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / -78 °C 2: N-Bromosuccinimide / N,N-dimethyl-formamide
	Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere 1.2: 16 h / -78 - 20 °C / Inert atmosphere 2.1: N-Bromosuccinimide; acetic acid / chloroform / 2 h / 0 - 20 °C

Reference： [1]Xia, Chuanjun; Fan, Xiaowu; Locklin, Jason; Advincula, Rigoberto C. [Organic Letters, 2002, vol. 4, # 12, p. 2067 - 2070]
[2]Matsumoto, Kouzou; Kugo, Sota; Takajo, Daisuke; Inaba, Akira; Hirao, Yasukazu; Kurata, Hiroyuki; Kawase, Takeshi; Kubo, Takashi [Chemistry - An Asian Journal, 2012, vol. 7, # 1, p. 225 - 232]
[3]Jing, Shan; Zhang, Ruilin; Dai, Heng; Du, Chao; Cheng, Xiaohong [Chinese Journal of Chemistry, 2012, vol. 30, # 3, p. 577 - 584]
[4]Kirkus, Mindaugas; Wang, Linjun; Mothy, Sebastien; Beljonne, David; Cornil, Jerome; Janssen, Rene A. J.; Meskers, Stefan C. J. [Journal of Physical Chemistry A, 2012, vol. 116, # 30, p. 7927 - 7936]
[5]Hwang, Min Ji; Park, Ji Hee; Jeong, Eun Bin; Kang, Il; Lee, Dong Hoon; Park, Chan Eon; Singh; Choi, Ho June; Kim, Yoon-Hi; Yoon, Yong Jin; Kwon, Soon-Ki; Lee, Sang-Gyeong [Bulletin of the Korean Chemical Society, 2012, vol. 33, # 11, p. 3810 - 3816]
[6]Lee, Che-Hsiung; Plunkett, Kyle N. [Organic Letters, 2013, vol. 15, # 6, p. 1202 - 1205]
[7]Gao, Lei; Zhang, Jing; He, Chang; Shen, Suling; Zhang, Yi; Liu, Hongtao; Sun, Qingjiang; Li, Yongfang [Science China Chemistry, 2013, vol. 56, # 7, p. 997 - 1003]
[8]Shaik, Baji; Park, Ji Hee; An, Tae Kyu; Noh, Young Ri; Yoon, Soon Byung; Park, Chan Eon; Yoon, Young Jin; Kim, Yun-Hi; Lee, Sang-Gyeong [Tetrahedron, 2013, vol. 69, # 38, p. 8191 - 8198]
[9]Kuo, Cheng-Yu; Nie, Wanyi; Tsai, Hsinhan; Yen, Hung-Ju; Mohite, Adytia D.; Gupta, Gautam; Dattelbaum, Andrew M.; William, Darrick J.; Cha, Kitty C.; Yang, Yang; Wang, Leeyih; Wang, Hsing-Lin [Macromolecules, 2014, vol. 47, # 3, p. 1008 - 1020]
[10]Lin, Chien-Min; Li, Ming-Shiou; Dwivedi, Atul Kumar; Lin, Hong-Cheu [Dyes and Pigments, 2018, vol. 157, p. 179 - 189]
[11]Yang, Xuan; Rominger, Frank; Mastalerz, Michael [Organic Letters, 2018, vol. 20, # 22, p. 7270 - 7273]

33
[ 211737-28-9 ]
((C₄H₄SC₆H₁₁)2C₄HS)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: Mg / diethyl ether 1.2: 90 percent / NidpppCl₂ / diethyl ether / 20 h / 20 °C 2.1: BuLi / tetrahydrofuran / 0.75 h / -78 °C 2.2: 54 percent / CuCl₂ / tetrahydrofuran / -78 - 20 °C

Reference： [1]Xia, Chuanjun; Fan, Xiaowu; Locklin, Jason; Advincula, Rigoberto C. [Organic Letters, 2002, vol. 4, # 12, p. 2067 - 2070]

34
[ 211737-28-9 ]
5,5''-Dihexyl-[2,2';5',2'']terthiophene 1,1,1'',1''-tetraoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 37 percent / m-CPBA / CH₂Cl₂ / Ambient temperature 2: 44 percent / Pd(AsPh₃)4 / toluene / 5 h / Heating

Reference： [1]Barbarella; Favaretto; Sotgiu; Zambianchi; Antolini; Pudova; Bongini [Journal of Organic Chemistry, 1998, vol. 63, # 16, p. 5497 - 5506]

35
[ 211737-28-9 ]
5,5'''-Dihexyl-[2,2';5',2'';5'',2''']quaterthiophene 1,1-dioxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) TMEDA, BuLi, 2.) Bu₃SnCl / 3.) Pd(PPh₃)4 / 1.) THF, hexane, room temperature, 3 h, 2.) -70 deg C to room temperature, 3.) toluene, reflux, overnight 2: 1.) BuLi, TMEDA, Bu₃SnCl / 2.) Pd(AsPh₃)4 / 1.) THF, hexane, room temperature, overnight, 2.) toluene, reflux, overnight
	Multi-step reaction with 2 steps 1: 37 percent / m-CPBA / CH₂Cl₂ / Ambient temperature 2: 1.) BuLi, TMEDA, Bu₃SnCl / 2.) Pd(AsPh₃)4 / 1.) THF, hexane, room temperature, overnight, 2.) toluene, reflux, overnight

Reference： [1]Barbarella; Favaretto; Sotgiu; Zambianchi; Antolini; Pudova; Bongini [Journal of Organic Chemistry, 1998, vol. 63, # 16, p. 5497 - 5506]
[2]Barbarella; Favaretto; Sotgiu; Zambianchi; Antolini; Pudova; Bongini [Journal of Organic Chemistry, 1998, vol. 63, # 16, p. 5497 - 5506]

36
[ 211737-28-9 ]
5,5''''-Dihexyl-[2,2';5',2'';5'',2''';5''',2'''']quinquethiophene 1,1,1'',1'',1'''',1''''-hexaoxide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 37 percent / m-CPBA / CH₂Cl₂ / Ambient temperature 2: 1.) Pd(PPh₃)4, 2.) Pd(AsPh₃)4 / 1.) toluene, reflux, 1 h, 2.) toluene, reflux, 4 h

Reference： [1]Barbarella; Favaretto; Sotgiu; Zambianchi; Antolini; Pudova; Bongini [Journal of Organic Chemistry, 1998, vol. 63, # 16, p. 5497 - 5506]

37
[ 211737-28-9 ]
[ 849138-20-1 ]
bis-(5'-hexylthiophen-2'-yl)-2,6-anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium carbonate In water; toluene at 90℃; for 72h;	6 To a solution of 2,6- anthracene-bis-4',4',5',5'-tetramethyl-1 ',3',2'-dioxaborolane (prepared as in Example 5, 6.8220 g, 15.86 mmol) and 2-bromo-5-hexylthophene (8.6251 g, 34.89 mmol) dissolved in toluene (240 ml) was added sodium carbonate (8.48 g, 80 mmol) dissolved in water (40 ml) followed by th e addition of phase-transfer agent Aliquat 336 (3.2 g, 8.0 mmol). The mixture was bubbled with nitrogen for 15 min. Then, tetrakis(triphenylphosphine)palladium(0) (368 mg, 2 % mol) was added. The mixture was heated to 90 0C for three days under a nitrogen atmosphere. The reaction mixture was cooled to room temperature and poured into methanol (600 ml). The yellow precipitate was filtered off, washed with water, dilute acid (5 % HCI), water, methanol, then with acetone (3x) to remove the starting material and mono-substituted by¬ product. The crude product was purified by sublimation (2Z0 °C/60 mmTorr) in a 3-zone furnace, followed by recrystallization from xylenes to give 4.2802 g (53%) of bright yellow product. 1H NMR (p-d ichlorobenzene- d4, 500 MHz): δ 8.15 ppm (s, 2 H), 8.01 ppm (s, 2 H), 7.82-7.80 ppm (d, 2 H, J = 8.5 Hz), 7.61-7.59 ppm (d, 2 H, J = 8.5 Hz ), 7.19 ppm (d, 2 H, J = 3.45 Hz), 7.02 ppm (d, 2 H, J = 3.45 Hz), 6.71 ppm (s, 2 H ), 2.80-2.77 ppm (t, 2 H, J = 8.6 Hz), 1.70 ppm (m, 2 H), 1.32 ppm (m, 6 H), 0.89 ppm (t, 3 H, J = 7.5 Hz);; 13C-NMR (CDCI3, 500 MHz): δ 146.6, 142.7, 132.8, 132.4, 132.2, 130.2, 129.3, 126.8, 125.9, 125.1 , 124.0, 32.36, 32.28, 31.11 , 29.64, 23.33, 14.63 ppm. El, MS m/z (%): 510 (100, M+); HRMS found: 510.241463. Compounds 9 - 15 were synthesized in a similar manner as that described for the synthesis of DHTAnt.

Reference： [1]Current Patent Assignee: DUPONT DE NEMOURS INC - WO2006/50496, 2006, A1 Location in patent: Page/Page column 42

38
[ 211737-28-9 ]
[ 147437-99-8 ]
C₂₂H₂₂OS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-5-hexylthiophene With magnesium Stage #2: 3-(thiophen-2-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 0 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran Further stages.;

Reference： [1]Amaladass; Kumar, Natarajan Senthil; Mohanakrishnan, Arasambattu K. [Tetrahedron, 2008, vol. 64, # 34, p. 7992 - 7998]

39
[ 211737-28-9 ]
[ 147437-99-8 ]
C₂₂H₂₄O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-5-hexylthiophene With magnesium Stage #2: 3-(thiophen-2-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 0 - 20℃; Stage #3: With ammonium chloride In tetrahydrofuran Further stages.;

Reference： [1]Amaladass; Kumar, Natarajan Senthil; Mohanakrishnan, Arasambattu K. [Tetrahedron, 2008, vol. 64, # 34, p. 7992 - 7998]

40
[ 211737-28-9 ]
[ 205643-78-3 ]
C₂₆H₂₄OS₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-5-hexylthiophene With magnesium Stage #2: 3-(2,2’-bithiophen-5-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 0 - 20℃; Stage #3: With hydrogenchloride In tetrahydrofuran Further stages.;

Reference： [1]Amaladass; Kumar, Natarajan Senthil; Mohanakrishnan, Arasambattu K. [Tetrahedron, 2008, vol. 64, # 34, p. 7992 - 7998]

41
[ 211737-28-9 ]
[ 205643-78-3 ]
C₂₆H₂₆O₂S₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-5-hexylthiophene With magnesium Stage #2: 3-(2,2’-bithiophen-5-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 0 - 20℃; Stage #3: With ammonium chloride In tetrahydrofuran Further stages.;

Reference： [1]Amaladass; Kumar, Natarajan Senthil; Mohanakrishnan, Arasambattu K. [Tetrahedron, 2008, vol. 64, # 34, p. 7992 - 7998]

42
[ 211737-28-9 ]
[ 4281-21-4 ]
C₃₆H₄₂O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-5-hexylthiophene With magnesium Stage #2: 3-(3-phthalidyl)phthalide In tetrahydrofuran at 0 - 20℃; Stage #3: With ammonium chloride In tetrahydrofuran Further stages.;

Reference： [1]Amaladass; Kumar, Natarajan Senthil; Mohanakrishnan, Arasambattu K. [Tetrahedron, 2008, vol. 64, # 34, p. 7992 - 7998]

43
[ 1115589-08-6 ]
[ 211737-28-9 ]
C₃₆H₄₁NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-5-hexylthiophene With magnesium Stage #2: 3-(9-hexyl-9H-carbazol-3-yl)isobenzofuran-1(3H)-one In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water