10-bromodecylbenzene

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

Procedure: To a 100 mL flask under nitrogen was added magnesium (486 mg, 20 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 10-bromodecylbenzene (5.95 g, 20 mmol) was added dropwise. The reaction mixture was kept under reflex temperatures until all magnesium was consumed. Subsequently, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) suspended in anhydrous THF (10 ml) was added dropwise. After refluxing for 3 hours more, it was cooled down to room temperature. SnCl2 solution (7.5 g in 19 mL 10% HCl) was slowly added dropwise and then the mixture was kept at 60° C. overnight. After cooling down, brine (25 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent and gave a pale yellow oil (466 mg, yield 15%), which turned into a solid upon standing for a few days. 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=6.0 Hz, 2H), 7.46 (d, J=5.0 Hz, 2H), 7.27-7.32 (m, 4H), 7.19 (d, J=7.0 Hz, 6H), 3.19 (t, J=8.0 Hz, 4H), 2.61 (t, J=7.5 Hz, 4H), 1.75-1.86 (m, 4H), 1.58-1.67 (m, 4H), 1.42-1.51 (m, 4H), 1.15-1.41 (m, 20H). The mixture was heated under reflux was consumed was added dropwise After refluxing for 3 hours more After cooling down The organic phase was separated dried over Na2SO4 The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent

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

Procedure: To a 250 mL flask in ice-water bath was added 1,10-dibromodecane (46.0 g, 153 mmol) and anhydrous THF (100 ml) under nitrogen. Phenyl lithium (1.8 M in dibutyl ether, 28.5 mL, 51 mmol) was added dropwise. After addition was completed, the reaction mixture was stirred for 1 hour and warmed to room temperature. After 48 hours, it was quenched with H2O (200 mL), extracted with CH2Cl2 (200 mL×2) and dried. After concentration, the residue was distilled to give a colorless oil (9.35 g, yield 61.7%) at 130° C./0.07 mmHg. 1H NMR (CDCl3, 500 MHz) δ=7.27-7.32 (m, 2H), 7.20 (d, J=6.5 Hz, 3H), 3.43 (t, J=7.0 Hz, 2H), 2.62 (t, J=8.0 Hz, 2H), 1.84-1.96 (m, 2H), 1.60-1.68 (m, 2H), 1.41-1.52 (m, 2H), 1.24-1.41 (m, 10H). After addition After 48 hours it was quenched with H2O (200 mL) extracted with CH2Cl2 (200 mL×2) dried After concentration the residue was distilled

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

Procedure: To a 100 mL flask under nitrogen was added magnesium (486 mg, 20 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 10-bromodecylbenzene (5.95 g, 20 mmol) was added dropwise. The reaction mixture was kept under reflex temperatures until all magnesium was consumed. Subsequently, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) suspended in anhydrous THF (10 ml) was added dropwise. After refluxing for 3 hours more, it was cooled down to room temperature. SnCl2 solution (7.5 g in 19 mL 10% HCl) was slowly added dropwise and then the mixture was kept at 60° C. overnight. After cooling down, brine (25 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent and gave a pale yellow oil (466 mg, yield 15%), which turned into a solid upon standing for a few days. 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=6.0 Hz, 2H), 7.46 (d, J=5.0 Hz, 2H), 7.27-7.32 (m, 4H), 7.19 (d, J=7.0 Hz, 6H), 3.19 (t, J=8.0 Hz, 4H), 2.61 (t, J=7.5 Hz, 4H), 1.75-1.86 (m, 4H), 1.58-1.67 (m, 4H), 1.42-1.51 (m, 4H), 1.15-1.41 (m, 20H). The mixture was heated under reflux was consumed was added dropwise After refluxing for 3 hours more After cooling down The organic phase was separated dried over Na2SO4 The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent

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

Procedure: To a 250 mL flask in ice-water bath was added 1,10-dibromodecane (46.0 g, 153 mmol) and anhydrous THF (100 ml) under nitrogen. Phenyl lithium (1.8 M in dibutyl ether, 28.5 mL, 51 mmol) was added dropwise. After addition was completed, the reaction mixture was stirred for 1 hour and warmed to room temperature. After 48 hours, it was quenched with H2O (200 mL), extracted with CH2Cl2 (200 mL×2) and dried. After concentration, the residue was distilled to give a colorless oil (9.35 g, yield 61.7%) at 130° C./0.07 mmHg. 1H NMR (CDCl3, 500 MHz) δ=7.27-7.32 (m, 2H), 7.20 (d, J=6.5 Hz, 3H), 3.43 (t, J=7.0 Hz, 2H), 2.62 (t, J=8.0 Hz, 2H), 1.84-1.96 (m, 2H), 1.60-1.68 (m, 2H), 1.41-1.52 (m, 2H), 1.24-1.41 (m, 10H). After addition After 48 hours it was quenched with H2O (200 mL) extracted with CH2Cl2 (200 mL×2) dried After concentration the residue was distilled

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

Procedure: To a 100 mL flask under nitrogen was added magnesium (486 mg, 20 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 10-bromodecylbenzene (5.95 g, 20 mmol) was added dropwise. The reaction mixture was kept under reflex temperatures until all magnesium was consumed. Subsequently, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) suspended in anhydrous THF (10 ml) was added dropwise. After refluxing for 3 hours more, it was cooled down to room temperature. SnCl2 solution (7.5 g in 19 mL 10% HCl) was slowly added dropwise and then the mixture was kept at 60° C. overnight. After cooling down, brine (25 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent and gave a pale yellow oil (466 mg, yield 15%), which turned into a solid upon standing for a few days. 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=6.0 Hz, 2H), 7.46 (d, J=5.0 Hz, 2H), 7.27-7.32 (m, 4H), 7.19 (d, J=7.0 Hz, 6H), 3.19 (t, J=8.0 Hz, 4H), 2.61 (t, J=7.5 Hz, 4H), 1.75-1.86 (m, 4H), 1.58-1.67 (m, 4H), 1.42-1.51 (m, 4H), 1.15-1.41 (m, 20H). The mixture was heated under reflux was consumed was added dropwise After refluxing for 3 hours more After cooling down The organic phase was separated dried over Na2SO4 The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent

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

Procedure: To a 250 mL flask in ice-water bath was added 1,10-dibromodecane (46.0 g, 153 mmol) and anhydrous THF (100 ml) under nitrogen. Phenyl lithium (1.8 M in dibutyl ether, 28.5 mL, 51 mmol) was added dropwise. After addition was completed, the reaction mixture was stirred for 1 hour and warmed to room temperature. After 48 hours, it was quenched with H2O (200 mL), extracted with CH2Cl2 (200 mL×2) and dried. After concentration, the residue was distilled to give a colorless oil (9.35 g, yield 61.7%) at 130° C./0.07 mmHg. 1H NMR (CDCl3, 500 MHz) δ=7.27-7.32 (m, 2H), 7.20 (d, J=6.5 Hz, 3H), 3.43 (t, J=7.0 Hz, 2H), 2.62 (t, J=8.0 Hz, 2H), 1.84-1.96 (m, 2H), 1.60-1.68 (m, 2H), 1.41-1.52 (m, 2H), 1.24-1.41 (m, 10H). After addition After 48 hours it was quenched with H2O (200 mL) extracted with CH2Cl2 (200 mL×2) dried After concentration the residue was distilled

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Compound 11 (7.0 g) was dissolved in toluene (80 mL) and triphenylphosphine (6.8 g) was added thereto, followed by stirring at 100° C. for 12 hours. Triphenylphosphine (1.3 g) was further added, followed by stirring at 100° C. for 24 hours. After cooling the reaction solution to room temperature, the resulting precipitate was washed with toluene three times and the residue was dried under reduced pressure to obtain the title compound (7.2 g) having the following physical property values. by stirring at 100° C. for 24 hours After cooling the reaction solution to room temperature the resulting precipitate was washed with toluene three times the residue was dried under reduced pressure

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

Procedure: In diethylether (200 mL), 10-phenyl-1-decanol (10 g) was dissolved, phosphorus tribromide (4.0 mL) was carefully added thereto, at 0° C., followed by stirring at room temperature for 6 hours. Water was added carefully to the reaction solution, followed by extraction with tert-buthylmethylether. The organic layer was washed with water, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to obtain the title compound (7.0 g) having the following physical property values. at 0° C. followed by extraction with tert-buthylmethylether The organic layer was washed with water dried with anhydrous sodium sulfate concentrated under reduced pressure The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

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

Procedure: To a 100 mL flask under nitrogen was added magnesium (486 mg, 20 mmol) and anhydrous THF (10 mL). The mixture was heated under reflux and 10-bromodecylbenzene (5.95 g, 20 mmol) was added dropwise. The reaction mixture was kept under reflex temperatures until all magnesium was consumed. Subsequently, 4,8-dihydrobenzo[1,2-b:4,5-b′]dithiophene-4,8-dione (1.1 g, 5.0 mmol) suspended in anhydrous THF (10 ml) was added dropwise. After refluxing for 3 hours more, it was cooled down to room temperature. SnCl2 solution (7.5 g in 19 mL 10% HCl) was slowly added dropwise and then the mixture was kept at 60° C. overnight. After cooling down, brine (25 mL) was added. The organic phase was separated and dried over Na2SO4. The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent and gave a pale yellow oil (466 mg, yield 15%), which turned into a solid upon standing for a few days. 1H NMR (CDCl3, 500 MHz) δ=7.48 (d, J=6.0 Hz, 2H), 7.46 (d, J=5.0 Hz, 2H), 7.27-7.32 (m, 4H), 7.19 (d, J=7.0 Hz, 6H), 3.19 (t, J=8.0 Hz, 4H), 2.61 (t, J=7.5 Hz, 4H), 1.75-1.86 (m, 4H), 1.58-1.67 (m, 4H), 1.42-1.51 (m, 4H), 1.15-1.41 (m, 20H). The mixture was heated under reflux was consumed was added dropwise After refluxing for 3 hours more After cooling down The organic phase was separated dried over Na2SO4 The residue after vacuum evaporation was purified by column chromatography with hexane/AcOEt 50:1 as eluent

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

Procedure: To a 250 mL flask in ice-water bath was added 1,10-dibromodecane (46.0 g, 153 mmol) and anhydrous THF (100 ml) under nitrogen. Phenyl lithium (1.8 M in dibutyl ether, 28.5 mL, 51 mmol) was added dropwise. After addition was completed, the reaction mixture was stirred for 1 hour and warmed to room temperature. After 48 hours, it was quenched with H2O (200 mL), extracted with CH2Cl2 (200 mL×2) and dried. After concentration, the residue was distilled to give a colorless oil (9.35 g, yield 61.7%) at 130° C./0.07 mmHg. 1H NMR (CDCl3, 500 MHz) δ=7.27-7.32 (m, 2H), 7.20 (d, J=6.5 Hz, 3H), 3.43 (t, J=7.0 Hz, 2H), 2.62 (t, J=8.0 Hz, 2H), 1.84-1.96 (m, 2H), 1.60-1.68 (m, 2H), 1.41-1.52 (m, 2H), 1.24-1.41 (m, 10H). After addition After 48 hours it was quenched with H2O (200 mL) extracted with CH2Cl2 (200 mL×2) dried After concentration the residue was distilled