3,5-DIBROMO-1-TRIMETHYLSILYLBENZENE

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to -68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar

反応条件: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate

反応条件: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar

反応条件: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate

反応条件: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate

反応条件: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar

反応条件: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate

反応条件: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within 20 minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25 (s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate

反応条件: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ 7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar

反応条件: temp:-55.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 42.4 g of Tribromobenzene (134.6 mmol) was dissolved in 600 mL Et2O. The solution was chilled to −55° C., at which temperature starting material precipitated. 54 mL of n-BuLi (2.5 M in hexanes, 135 mmol) were added within minutes. After stirring for 35 minutes at −52° C., 20 ml TMSCl (158 mmol) and 20 mL Et2O were added within 7 minutes. The suspension turned into a solution at −42° C., and a fine precipitate appeared at −30° C. The suspension was stirred overnight at room temperature. 100 mL 2M HCl were used to hydrolyze the mixture. After stirring for 30 minutes, the Et2O-phase was dried with MgSO4, filtered, and solvent evaporated until compound crystallized out of solution. The flask was stored overnight at +4° C. The crystalline compound was filtered, washed with a small amount cold pentane, and dried under vacuo. A second fraction of crystalline compound was obtained from the filtrate. Yield: 31.9 g (103.5 mmol, 77%). 1H-NMR (CHCl3=7.24 ppm): δ 7.62 (t, 1H), 7.49 (d, 2H), 0.25(s, 3×3H). precipitated turned into a solution at −42° C. appeared at −30° C The suspension was stirred overnight at room temperature After stirring for 30 minutes the Et2O-phase was dried with MgSO4 filtered solvent evaporated until compound crystallized out of solution The flask was stored overnight at +4° C The crystalline compound was filtered washed with a small amount cold pentane dried under vacuo A second fraction of crystalline compound was obtained from the filtrate

反応条件: temp:-68.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 17.18 g of 3,5-Dibromo-trimethylsilyl-benzene, 55.8 mmol, was dissolved in 380 ml Et2O. The solution was chilled to −68° C., and 22.3 mL of n-BuLi (2.5 M in hexanes), 55.8 mmol, were added within 18 minutes. The solution changed its color from clear to yellow, and was stirred for 45 minutes at −68° C. 7.5 mL TMSCl, 59 mmol, were added within six minutes. The temperature of solution rose within one hour to −33° C., and after another 30 minutes to −18° C. The solution was stirred overnight at room temperature. 60 mL of 2M HCl were added to the white suspension. Stirring for 30 minutes resulted in two clear phases. Et2O-phase was dried with MgSO4, filtered, and solvent evaporated. Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar. All pure fractions were combined and gave 15.8 g of product (52.4 mmol, 94%). 1H-NMR (CHCl3=7.24 ppm): δ7.56 (s, 2H), 7.50 (t, 1H), 0.25 (s, 6×3H). The solution was stirred overnight at room temperature Stirring for 30 minutes resulted in two clear phases Et2O-phase was dried with MgSO4 filtered solvent evaporated Raw product was distilled at a temperature of 70-76° C. and 0.1-0.2 mbar