dichloro(dihexyl)silane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dichlorosilane in an amount of 83.5 g (0.827 mol), 88.6 g of 1-hexene (1.08 mol) and 0.05 mol % of chloroplatinic acid (relative to dichlorosilane) were charged in a stainless steel reactor and sealed and subjected to reaction in a bath at a temperature of 50° C. for 5 hours. After reaction, the seal of the reactor was broken and the reacted liquid was discharged, and by vacuum distillation, n-hexyldichlorosilane was obtained with a yield of 18% and di-n-hexyldichlorosilane with a yield of 72%. sealed subjected to reaction in a bath at a temperature of 50° C. for 5 hours After reaction the seal of the reactor by vacuum distillation

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dichlorosilane in an amount of 83.5 g (0.827 mol), 88.6 g of 1-hexene (1.08 mol) and 0.05 mol % of chloroplatinic acid (relative to dichlorosilane) were charged in a stainless steel reactor and sealed and subjected to reaction in a bath at a temperature of 50° C. for 5 hours. After reaction, the seal of the reactor was broken and the reacted liquid was discharged, and by vacuum distillation, n-hexyldichlorosilane was obtained with a yield of 18% and di-n-hexyldichlorosilane with a yield of 72%. sealed subjected to reaction in a bath at a temperature of 50° C. for 5 hours After reaction the seal of the reactor by vacuum distillation

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of n-BuLi in hexane (60 mmol, 24 mL) in anhydrous THF (500 mL) at −78° C. was added dropwise under vigorous stirring a solution of 11 (30 mmol, 9.720 g) in anhydrous THF (100 mL) over 30 min. The mixture was then stirred at −78° C. for 1 h, resulting in a white suspension. Next, a solution of dichlorodihexylsilane (30 mmol, 8.070 g) in THF (100 mL) was added dropwise. The reaction mixture was stirred at −78° C. for five additional hours, allowed to warm to room temperature, and stirred overnight. The reaction was next quenched by adding saturated aqueous NH4Cl solution (300 mL). The aqueous layer was extracted with ether (3×100 mL). The organic phases were then combined and washed with water and dried over MgSO4. After filtration, the solvent was removed, and the crude product was purified by column chromatography to yield a light yellow liquid (6.8 g, 68%). 1H NMR (CDCl3): δ 0.85-0.93 (m, 10H), 1.24-1.41 (m, 16H), 7.06 (d, 2H, J=5 Hz), 7.21 (d, 2H, J=5 Hz) ppm; 13C NMR (CDCl3): δ 12.07, 14.29, 22.80, 24.37, 31.65, 33.07, 125.17, 126.85, 141.81, 149.37 ppm. resulting in a white suspension The reaction mixture was stirred at −78° C. for five additional hours to warm to room temperature stirred overnight The reaction was next quenched by adding saturated aqueous NH4Cl solution (300 mL) The aqueous layer was extracted with ether (3×100 mL) washed with water dried over MgSO4 After filtration the solvent was removed the crude product was purified by column chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,3′-dibromo-5,5′-bis(trimethylsilyl)-2,2′-bithiophene (Compound E4, synthesized in accordance with WO 2010/136353, 10.0 g) was placed in a 200 mL four-necked flask in a nitrogen atmosphere, and dissolved in tetrahydrofuran (150 mL). This was cooled to −78° C., and a solution of n-butyl lithium in hexane (KANTO CHEMICAL CO., INC., 1.64 M, 27.5 mL) was added dropwise. After about 30 minutes of agitation, dichlorodi-n-hexylsilane (5.7 g) was added dropwise. The temperature was gradually raised to room temperature over the course of about 2 hours, after which water was added, and the product was extracted with hexane. The organic layer was washed with water, dried with anhydrous sodium sulfate, and concentrated by filtration. The resulting yellow-orange oily substance was dissolved in hexane (100 mL) and chloroform (50 mL), trifluoroacetic acid (5 mL) with the internal temperature at 2° C., and after 10 minutes of agitation water was added, and the organic layer was washed, dried with anhydrous sodium sulfate, and then concentrated by filtration. Heptane (70 mL) was added to the reaction solution, which was then concentrated under reduced pressure. The resulting yellow-green oily substance was dissolved in hexane, and subjected to silica gel column chromatography (solvent: hexane) to obtain the target 4,4-di-n-hexyl-dithieno[3,2-b:2′,3′-d]silole (Compound E19, 7.1 g, yield 91%). The temperature was gradually raised to room temperature over the course of about 2 hours the product was extracted with hexane The organic layer was washed with water dried with anhydrous sodium sulfate concentrated by filtration The resulting yellow-orange oily substance was dissolved in hexane (100 mL) chloroform (50 mL), trifluoroacetic acid (5 mL) with the internal temperature at 2° C., and after 10 minutes of agitation water was added the organic layer was washed dried with anhydrous sodium sulfate concentrated by filtration Heptane (70 mL) was added to the reaction solution, which was then concentrated under reduced pressure The resulting yellow-green oily substance was dissolved in hexane

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3,3′-dibromo-5,5′-bis(trimethylsilyl)-2,2′-bithiophene (Compound E4, synthesized in accordance with WO 2010/136353, 10.0 g) was placed in a 200 mL four-necked flask in a nitrogen atmosphere, and dissolved in tetrahydrofuran (150 mL). This was cooled to −78° C., and a solution of n-butyl lithium in hexane (KANTO CHEMICAL CO., INC., 1.64 M, 27.5 mL) was added dropwise. After about 30 minutes of agitation, dichlorodi-n-hexylsilane (5.7 g) was added dropwise. The temperature was gradually raised to room temperature over the course of about 2 hours, after which water was added, and the product was extracted with hexane. The organic layer was washed with water, dried with anhydrous sodium sulfate, and concentrated by filtration. The resulting yellow-orange oily substance was dissolved in hexane (100 mL) and chloroform (50 mL), trifluoroacetic acid (5 mL) with the internal temperature at 2° C., and after 10 minutes of agitation water was added, and the organic layer was washed, dried with anhydrous sodium sulfate, and then concentrated by filtration. Heptane (70 mL) was added to the reaction solution, which was then concentrated under reduced pressure. The resulting yellow-green oily substance was dissolved in hexane, and subjected to silica gel column chromatography (solvent: hexane) to obtain the target 4,4-di-n-hexyl-dithieno[3,2-b:2′,3′-d]silole (Compound E19, 7.1 g, yield 91%). The temperature was gradually raised to room temperature over the course of about 2 hours the product was extracted with hexane The organic layer was washed with water dried with anhydrous sodium sulfate concentrated by filtration The resulting yellow-orange oily substance was dissolved in hexane (100 mL) chloroform (50 mL), trifluoroacetic acid (5 mL) with the internal temperature at 2° C., and after 10 minutes of agitation water was added the organic layer was washed dried with anhydrous sodium sulfate concentrated by filtration Heptane (70 mL) was added to the reaction solution, which was then concentrated under reduced pressure The resulting yellow-green oily substance was dissolved in hexane

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 9.2 g (70.7 mmoles) of 2-methylindene are introduced into 200 mL of toluene and 15 mL of THF, and 28.3 mL of n-butyllithium (2.5 M in toluene) are added without interruption at room temperature. After this addition is complete, the mixture is heated to 80° C. and stirred at this temperature for one hour. It is allowed to cool to 40° C., then 9.5 g (35.4 mmoles) of di-n-hexyldichlorosilane are slowly added dropwise. After this addition, the reaction solution is stirred for three hours at 60° C. and then overnight at room temperature. 80 mL of water are added and the phases that form are separated. The organic phase is washed with 100 mL of water, and the aqueous phase is extracted three times with a total of 100 mL of toluene. The combined organic phases are dried over magnesium sulfate. After separation of the magnesium sulfate, the solvent is removed and the residue is purified by column chromatography. The desired product is isolated in a yield of 13.3 g (82%) (purity 99%). are added without interruption at room temperature After this addition to cool to 40° C. After this addition the reaction solution is stirred for three hours at 60° C. overnight at room temperature the phases that form are separated The organic phase is washed with 100 mL of water the aqueous phase is extracted three times with a total of 100 mL of toluene The combined organic phases are dried over magnesium sulfate After separation of the magnesium sulfate the solvent is removed the residue is purified by column chromatography

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of n-BuLi in hexane (60 mmol, 24 mL) in anhydrous THF (500 mL) at −78° C. was added dropwise under vigorous stirring a solution of 11 (30 mmol, 9.720 g) in anhydrous THF (100 mL) over 30 min. The mixture was then stirred at −78° C. for 1 h, resulting in a white suspension. Next, a solution of dichlorodihexylsilane (30 mmol, 8.070 g) in THF (100 mL) was added dropwise. The reaction mixture was stirred at −78° C. for five additional hours, allowed to warm to room temperature, and stirred overnight. The reaction was next quenched by adding saturated aqueous NH4Cl solution (300 mL). The aqueous layer was extracted with ether (3×100 mL). The organic phases were then combined and washed with water and dried over MgSO4. After filtration, the solvent was removed, and the crude product was purified by column chromatography to yield a light yellow liquid (6.8 g, 68%). 1H NMR (CDCl3): δ 0.85-0.93 (m, 10H), 1.24-1.41 (m, 16H), 7.06 (d, 2H, J=5 Hz), 7.21 (d, 2H, J=5 Hz) ppm; 13C NMR (CDCl3): δ 12.07, 14.29, 22.80, 24.37, 31.65, 33.07, 125.17, 126.85, 141.81, 149.37 ppm. resulting in a white suspension The reaction mixture was stirred at −78° C. for five additional hours to warm to room temperature stirred overnight The reaction was next quenched by adding saturated aqueous NH4Cl solution (300 mL) The aqueous layer was extracted with ether (3×100 mL) washed with water dried over MgSO4 After filtration the solvent was removed the crude product was purified by column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dichlorosilane in an amount of 83.5 g (0.827 mol), 88.6 g of 1-hexene (1.08 mol) and 0.05 mol % of chloroplatinic acid (relative to dichlorosilane) were charged in a stainless steel reactor and sealed and subjected to reaction in a bath at a temperature of 50° C. for 5 hours. After reaction, the seal of the reactor was broken and the reacted liquid was discharged, and by vacuum distillation, n-hexyldichlorosilane was obtained with a yield of 18% and di-n-hexyldichlorosilane with a yield of 72%. sealed subjected to reaction in a bath at a temperature of 50° C. for 5 hours After reaction the seal of the reactor by vacuum distillation