1-ethenyl-4-iodobenzene

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

Procedure: A solution of butyl lithium in ether was obtained by reacting a solution consisting of 137 g of butyl bromide and 200 ml of ether with a suspension consisting of 17 g of lithium and 400 ml of ether by the use of the same apparatus as that used in Referential Example 1. This solution was added dropwise to 300 ml of an ether solution containing 180 g of 9-bromoacridine at 0°-5° C., and the mixture was then warmed gradually to room temperature and stirred for further 3 hours. To the mixture was added dropwise 322 g of p-iodostyrene diluted with 300 ml of ether in the presence of cobalt chloride with stirring in a nitrogen gas stream, and the mixture was then refluxed for 5 hours. The reaction mixture was poured onto hydrochloric acid-ice and stirred. The organic layer was extracted with ether, and the extract was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain yellowish white crystals. The crystals were purified by alumina column chromatography to obtain 75.6 g of 9-(p-vinylphenyl)acridine, yield 38.4%. with stirring in a nitrogen gas stream the mixture was then refluxed for 5 hours The reaction mixture was poured onto hydrochloric acid-ice stirred The organic layer was extracted with ether the extract was dried over anhydrous sodium sulfate The solvent was then distilled off to obtain yellowish white crystals The crystals were purified by alumina column chromatography

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

Procedure: A solution of butyl lithium in ether was obtained by reacting a solution consisting of 137 g of butyl bromide and 200 ml of ether with a suspension consisting of 17 g of lithium and 400 ml of ether by the use of the same apparatus as that used in Referential Example 1. This solution was added dropwise to 300 ml of an ether solution containing 180 g of 9-bromoacridine at 0°-5° C., and the mixture was then warmed gradually to room temperature and stirred for further 3 hours. To the mixture was added dropwise 322 g of p-iodostyrene diluted with 300 ml of ether in the presence of cobalt chloride with stirring in a nitrogen gas stream, and the mixture was then refluxed for 5 hours. The reaction mixture was poured onto hydrochloric acid-ice and stirred. The organic layer was extracted with ether, and the extract was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain yellowish white crystals. The crystals were purified by alumina column chromatography to obtain 75.6 g of 9-(p-vinylphenyl)acridine, yield 38.4%. with stirring in a nitrogen gas stream the mixture was then refluxed for 5 hours The reaction mixture was poured onto hydrochloric acid-ice stirred The organic layer was extracted with ether the extract was dried over anhydrous sodium sulfate The solvent was then distilled off to obtain yellowish white crystals The crystals were purified by alumina column chromatography

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

Procedure: A solution of butyl lithium in ether was obtained by reacting a solution consisting of 137 g of butyl bromide and 200 ml of ether with a suspension consisting of 17 g of lithium and 400 ml of ether by the use of the same apparatus as that used in Referential Example 1. This solution was added dropwise to 300 ml of an ether solution containing 180 g of 9-bromoacridine at 0°-5° C., and the mixture was then warmed gradually to room temperature and stirred for further 3 hours. To the mixture was added dropwise 322 g of p-iodostyrene diluted with 300 ml of ether in the presence of cobalt chloride with stirring in a nitrogen gas stream, and the mixture was then refluxed for 5 hours. The reaction mixture was poured onto hydrochloric acid-ice and stirred. The organic layer was extracted with ether, and the extract was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain yellowish white crystals. The crystals were purified by alumina column chromatography to obtain 75.6 g of 9-(p-vinylphenyl)acridine, yield 38.4%. with stirring in a nitrogen gas stream the mixture was then refluxed for 5 hours The reaction mixture was poured onto hydrochloric acid-ice stirred The organic layer was extracted with ether the extract was dried over anhydrous sodium sulfate The solvent was then distilled off to obtain yellowish white crystals The crystals were purified by alumina column chromatography

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

Procedure: To an ice-cooled suspension of NaH (0.792 g, 33.0 mmol) in anhydrous 1,2-dimethoxyethane (20 mL) was added dropwise via syringe a solution of malononitrile (0.99 g, 15 mmol) in anhydrous 1,2-dimethoxyethane (5 mL) under N2. The mixture was stirred for 1 h at room temperature under N2. Next, 1-iodo-4-vinyl-benzene (1.15 g, 5.00 mmol), dry THF (15 mL), and tetrakis(triphenyphosphine)palladium(0) (0.58 g, 0.50 mmol) were added to the resulting pink suspension under an N2 flow, and the reaction mixture stirred at 85° C. for 2 h. After cooling to room temperature, the reaction mixture was poured into ice, neutralized with 10% HCl, and extracted with CH2Cl2 (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane: CH2Cl2, to give 0.603 g (71.8%) of the title compound as pale yellow solid: mp 40-42° C. ° C.; 1H NMR (400 MHz, CDCl3): δ 7.526 (d, 2H, J=7.6 Hz), 7.462 (d, 2H, J=7.6 Hz), 6.738 (d×d, 1H, J1=17.6 Hz, J2=10.8 Hz), 5.846 (d, 1H, J=17.6 Hz), 5.398 (d, 1H, J=10.8 Hz), 5.075 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 139.840, 135.372, 127.766, 127.556, 125.245, 116.619, 111.897, 28.050; Anal. Calcd. for C11H8N2: C, 78.55; H, 4.79; N, 16.66. Found; C, 78.76; H, 4.75; N, 16.02. the reaction mixture stirred at 85° C. for 2 h After cooling to room temperature the reaction mixture was poured into ice extracted with CH2Cl2 (100 mL) The organic layer was separated dried over anhydrous Na2SO4 concentrated in vacuo The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane

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

Procedure: To an ice-cooled suspension of NaH (0.792 g, 33.0 mmol) in anhydrous 1,2-dimethoxyethane (20 mL) was added dropwise via syringe a solution of malononitrile (0.99 g, 15 mmol) in anhydrous 1,2-dimethoxyethane (5 mL) under N2. The mixture was stirred for 1 h at room temperature under N2. Next, 1-iodo-4-vinyl-benzene (1.15 g, 5.00 mmol), dry THF (15 mL), and tetrakis(triphenyphosphine)palladium(0) (0.58 g, 0.50 mmol) were added to the resulting pink suspension under an N2 flow, and the reaction mixture stirred at 85° C. for 2 h. After cooling to room temperature, the reaction mixture was poured into ice, neutralized with 10% HCl, and extracted with CH2Cl2 (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane: CH2Cl2, to give 0.603 g (71.8%) of the title compound as pale yellow solid: mp 40-42° C. ° C.; 1H NMR (400 MHz, CDCl3): δ 7.526 (d, 2H, J=7.6 Hz), 7.462 (d, 2H, J=7.6 Hz), 6.738 (d×d, 1H, J1=17.6 Hz, J2=10.8 Hz), 5.846 (d, 1H, J=17.6 Hz), 5.398 (d, 1H, J=10.8 Hz), 5.075 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 139.840, 135.372, 127.766, 127.556, 125.245, 116.619, 111.897, 28.050; Anal. Calcd. for C11H8N2: C, 78.55; H, 4.79; N, 16.66. Found; C, 78.76; H, 4.75; N, 16.02. the reaction mixture stirred at 85° C. for 2 h After cooling to room temperature the reaction mixture was poured into ice extracted with CH2Cl2 (100 mL) The organic layer was separated dried over anhydrous Na2SO4 concentrated in vacuo The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane

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

Procedure: To an ice-cooled suspension of NaH (0.792 g, 33.0 mmol) in anhydrous 1,2-dimethoxyethane (20 mL) was added dropwise via syringe a solution of malononitrile (0.99 g, 15 mmol) in anhydrous 1,2-dimethoxyethane (5 mL) under N2. The mixture was stirred for 1 h at room temperature under N2. Next, 1-iodo-4-vinyl-benzene (1.15 g, 5.00 mmol), dry THF (15 mL), and tetrakis(triphenyphosphine)palladium(0) (0.58 g, 0.50 mmol) were added to the resulting pink suspension under an N2 flow, and the reaction mixture stirred at 85° C. for 2 h. After cooling to room temperature, the reaction mixture was poured into ice, neutralized with 10% HCl, and extracted with CH2Cl2 (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane:CH2Cl2, to give 0.603 g (71.8%) of the title compound as pale yellow solid: mp 40-42° C. ° C.; 1H NMR (400 MHz, CDCl3): δ 7.526 (d, 2H, J=7.6 Hz), 7.462 (d, 2H, J=7.6 Hz), 6.738 (d×d, 1H, J=17.6 Hz, J2=10.8 Hz), 5.846 (d, 1H, J=17.6 Hz), 5.398 (d, 1H, J=10.8 Hz), 5.075 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 139.840, 135.372, 127.766, 127.556, 125.245, 116.619, 111.897, 28.050; Anal. Calcd. for C11H8N2: C, 78.55; H, 4.79; N, 16.66. Found; C, 78.76; H, 4.75; N, 16.02. the reaction mixture stirred at 85° C. for 2 h After cooling to room temperature the reaction mixture was poured into ice extracted with CH2Cl2 (100 mL) The organic layer was separated dried over anhydrous Na2SO4 concentrated in vacuo The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane

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

Procedure: To an ice-cooled suspension of NaH (0.792 g, 33.0 mmol) in anhydrous 1,2-dimethoxyethane (20 mL) was added dropwise via syringe a solution of malononitrile (0.99 g, 15 mmol) in anhydrous 1,2-dimethoxyethane (5 mL) under N2. The mixture was stirred for 1 h at room temperature under N2. Next, 1-iodo-4-vinyl-benzene (1.15 g, 5.00 mmol), dry THF (15 mL), and tetrakis(triphenyphophine)palladium(0) (0.58g, 0.50 mmol) were added to the resulting pink suspension under an N2 flow, and the reaction mixture stirred at 85° C. for 2 h. After cooling to room temperature, the reaction mixture was poured into ice, neutralized with 10% HCl, and extracted with CH2Cl2 (100 mL). The organic layer was separated, dried over anhydrous Na2SO4, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane: CH2Cl2, to give 0.603 g (71.8%) of the title compound as pale yellow solid: mp 40-42° C. ° C; 1H NMR (400 MHz, CDCl3): δ 7.526 (d, 2H, J=7.6 Hz), 7.462 (d, 2H, J=7.6 Hz), 6.738 (d×d, 1H, J1=17.6 Hz, J2=10.8 Hz), 5.846 (d, 1H, J=17.6 Hz), 5.398 (d, 1H, J=10.8 Hz), 5.075 (s, 1H); 13C NMR (100 MHz, CDCl3): δ 139.840, 135.372, 127.766, 127.556, 125.245, 116.619, 111.897, 28.050; Anal. Calcd. for C11H8N2: C, 78.55; H, 4.79; N, 16.66. Found; C, 78.76; H, 4.75; N, 16.02. the reaction mixture stirred at 85° C. for 2 h After cooling to room temperature the reaction mixture was poured into ice extracted with CH2Cl2 (100 mL) The organic layer was separated dried over anhydrous Na2SO4 concentrated in vacuo The crude product was then purified by flash chromatography on silica gel eluting with 1:1 hexane

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

Procedure: A solution of butyl lithium in ether was obtained by reacting a solution consisting of 137 g of butyl bromide and 200 ml of ether with a suspension consisting of 17 g of lithium and 400 ml of ether by the use of the same apparatus as that used in Referential Example 1. This solution was added dropwise to 300 ml of an ether solution containing 180 g of 9-bromoacridine at 0°-5° C., and the mixture was then warmed gradually to room temperature and stirred for further 3 hours. To the mixture was added dropwise 322 g of p-iodostyrene diluted with 300 ml of ether in the presence of cobalt chloride with stirring in a nitrogen gas stream, and the mixture was then refluxed for 5 hours. The reaction mixture was poured onto hydrochloric acid-ice and stirred. The organic layer was extracted with ether, and the extract was dried over anhydrous sodium sulfate. The solvent was then distilled off to obtain yellowish white crystals. The crystals were purified by alumina column chromatography to obtain 75.6 g of 9-(p-vinylphenyl)acridine, yield 38.4%. with stirring in a nitrogen gas stream the mixture was then refluxed for 5 hours The reaction mixture was poured onto hydrochloric acid-ice stirred The organic layer was extracted with ether the extract was dried over anhydrous sodium sulfate The solvent was then distilled off to obtain yellowish white crystals The crystals were purified by alumina column chromatography