2-(3,5-二氯苯基)乙炔基]三甲基硅烷

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (3,5-dichloro-phenylethynyl)-trimethylsilane (4.85 g, 19.9 mmol) in methanol (50 mL) was added 1M potassium hydroxide (30 mL). The reaction mixture was stirred 1 h at room temperature and evaporated. The residue was treated with water (10 mL) and extracted with 3×40 mL diethyl ether. The tried organic phases were evaporated to give the desired 1,3-dichloro-5-ethynyl-benzene product in 2.3 g yield. evaporated The residue was treated with water (10 mL) extracted with 3×40 mL diethyl ether The tried organic phases were evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1,3-dichloro-5-iodo-benzene (5.44 g, 20 mmol) in diethylamine (75 mL) was added PdCl2(PPh3)2 (280 mg, 0.4 mmol), trimethylsilylacetylene (2.36 g, 24.0 mmol) and copper(I)iodide (20 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 24 h, filtered and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (8:2) as eluent. The desired (3,5-dichloro-phenylethynyl)-trimethylsilane product was isolated in 4.85 g yield. filtered evaporated The residue was purified by column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (3,5-dichloro-phenylethynyl)-trimethylsilane (4.85 g, 19.9 mmol) in methanol (50 mL) was added 1M potassium hydroxide (30 mL). The reaction mixture was stirred 1 h at room temperature and evaporated. The residue was treated with water (10 mL) and extracted with 3×40 mL diethyl ether. The tried organic phases were evaporated to give the desired 1,3-dichloro-5-ethynyl-benzene product in 2.3 g yield. evaporated The residue was treated with water (10 mL) extracted with 3×40 mL diethyl ether The tried organic phases were evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1,3-dichloro-5-iodo-benzene (5.44 g, 20 mmol) in diethylamine (75 mL) was added PdCl2(PPh3)2 (280 mg, 0.4 mmol), trimethylsilylacetylene (2.36 g, 24.0 mmol) and copper(I)iodide (20 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 24 h, filtered and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (8:2) as eluent. The desired (3,5-dichloro-phenylethynyl)-trimethylsilane product was isolated in 4.85 g yield. filtered evaporated The residue was purified by column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1,3-dichloro-5-iodo-benzene (5.44 g, 20 mmol) in diethylamine (75 mL) was added PdCl2(PPh3)2 (280 mg, 0.4 mmol), trimethylsilylacetylene (2.36 g, 24.0 mmol) and copper(I)iodide (20 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 24 h, filtered and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (8:2) as eluent. The desired (3,5-dichloro-phenylethynyl)-trimethylsilane product was isolated in 4.85 g yield. filtered evaporated The residue was purified by column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (3,5-dichloro-phenylethynyl)-trimethyl-silane (1.97 g, 8.1 mmol) in methanol (40 mL) was added a solution of potassium hydroxide (6.8 mg, 0.12 mmol) in H2O (0.24 mL). After stirring at ambient temperature for 40 minutes, the reaction mixture was diluted with water (40 mL), and extracted with hexane until the extracting solvent showing no product by TLC. The combined organic layer was dried over MgSO4, and concentrated to give the title compound (1.21 g, 87% yield) as a white solid. 1H NMR (CDCl3) δ 7.37-7.34 (m, 3H), 3.15 (s, 1H). extracted with hexane until the extracting solvent The combined organic layer was dried over MgSO4 concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (3,5-dichloro-phenylethynyl)-trimethyl-silane (1.97 g, 8.1 mmol) in methanol (40 mL) was added a solution of potassium hydroxide (6.8 mg, 0.12 mmol) in H2O (0.24 mL). After stirring at ambient temperature for 40 minutes, the reaction mixture was diluted with water (40 mL), and extracted with hexane until the extracting solvent showing no product by TLC. The combined organic layer was dried over MgSO4, and concentrated to give the title compound (1.21 g, 87% yield) as a white solid. 1H NMR (CDCl3) δ 7.37-7.34 (m, 3H), 3.15 (s, 1H). extracted with hexane until the extracting solvent The combined organic layer was dried over MgSO4 concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (3,5-dichloro-phenylethynyl)-trimethylsilane (4.85 g, 19.9 mmol) in methanol (50 mL) was added 1 M potassium hydroxide (30 mL). The reaction mixture was stirred 1 h at room temperature and evaporated. The residue was treated with water (10 mL) and extracted with 3×40 mL diethyl ether. The tried organic phases were evaporated to give the desired 1,3-dichloro-5-ethynyl-benzene product in 2.3 g yield. evaporated The residue was treated with water (10 mL) extracted with 3×40 mL diethyl ether The tried organic phases were evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1,3-dichloro-5-iodo-benzene (5.44 g, 20 mmol) in diethylamine (75 mL) was added PdCl2(PPh3)2 (280 mg, 0.4 mmol), trimethylsilylacetylene (2.36 g, 24.0 mmol) and copper(I)iodide (20 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 24 h, filtered and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (8:2) as eluent. The desired (3,5-dichlorophenylethynyl)-trimethyl-silane product was isolated in 4.85 g yield. filtered evaporated The residue was purified by column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (3,5-dichloro-phenylethynyl)-trimethylsilane (4.85 g, 19.9 mmol) in methanol (50 mL) was added 1M potassium hydroxide (30 mL). The reaction mixture was stirred 1 h at room temperature and evaporated. The residue was treated with water (10 mL) and extracted with 3×40 mL diethyl ether. The tried organic phases were evaporated to give the desired 1,3-dichloro-5-ethynyl-benzene product in 2.3 g yield. evaporated The residue was treated with water (10 mL) extracted with 3×40 mL diethyl ether The tried organic phases were evaporated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 1,3-dichloro-5-iodo-benzene (5.44 g, 20 mmol) in diethylamine (75 mL) was added PdCl2(PPh3)2 (280 mg, 0.4 mmol), trimethylsilylacetylene (2.36 g, 24.0 mmol) and copper(I)iodide (20 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 24 h, filtered and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (8:2) as eluent. The desired (3,5-dichloro-phenylethynyl)-trimethylsilane product was isolated in 4.85 g yield. filtered evaporated The residue was purified by column chromatography

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of (3,5-dichloro-phenylethynyl)-trimethyl-silane (1.97 g, 8.1 mmol) in methanol (40 mL) was added a solution of potassium hydroxide (6.8 mg, 0.12 mmol) in H2O (0.24 mL). After stirring at ambient temperature for 40 minutes, the reaction mixture was diluted with water (40 mL), and extracted with hexane until the extracting solvent showing no product by TLC. The combined organic layer was dried over MgSO4, and concentrated to give the title compound (1.21 g, 87% yield) as a white solid. 1H NMR (CDCl3) δ 7.37-7.34 (m, 3H), 3.15 (s, 1H). extracted with hexane until the extracting solvent The combined organic layer was dried over MgSO4 concentrated