trimethyl-(2-trimethylsilylphenyl)silane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium (9.72 g, 400 mmol), hexamethylphosphoramide (HMPA) (80 mL, 460 mmol), 1,2-dichlorobenzene (14.76 g, 100 mmol), and a catalytic amount of I2 were combined in a 500 mL round bottomed flask and heated to 70° C. with stirring. Chlorotrimethylsilane was added dropwise to the solution at 70° C. The solution was stirred for an additional 30 minutes and then heated to 100° C. for 48 h. After cooling, the reaction mixture was poured over ice and NaHCO3. The Mg and precipitate were filtered off and the filtrate was extracted with ether (3×, 200 mL). The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) and dried with Na2SO4 and concentrated. The product was distilled under reduced pressure at 128-133° C. to yield a light yellow oil (12.0426 g, 54.13%). 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 7.49 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 0.55 (s, 18H, CH3); 13C NMR (300 MHz, CDCl3) δ 145.98, 135.17, 127.76, 1.96 The solution was stirred for an additional 30 minutes heated to 100° C. for 48 h After cooling The Mg and precipitate were filtered off the filtrate was extracted with ether (3×, 200 mL) The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) dried with Na2SO4 concentrated The product was distilled under reduced pressure at 128-133° C.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium (9.72 g, 400 mmol), hexamethylphosphoramide (HMPA) (80 mL, 460 mmol), 1,2-dichlorobenzene (14.76 g, 100 mmol), and a catalytic amount of 12 were combined in a 500 mL round bottomed flask and heated to 70° C. with stirring. Chlorotrimethylsilane was added dropwise to the solution at 70° C. The solution was stirred for an additional 30 minutes and then heated to 100° C. for 48 h. After cooling, the reaction mixture was poured over ice and NaHCO3. The Mg and precipitate were filtered off and the filtrate was extracted with ether (3×, 200 mL). The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) and dried with Na2SO4 and concentrated. The product was distilled under reduced pressure at 128-133° C. to yield a light yellow oil (12.0426 g, 54.13%). 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 7.49 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 0.55 (s, 18H, CH3); 13C NMR (300 MHz, CDCl3) δ 145.98, 135.17, 127.76, 1.96 The solution was stirred for an additional 30 minutes heated to 100° C. for 48 h After cooling The Mg and precipitate were filtered off the filtrate was extracted with ether (3×, 200 mL) The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) dried with Na2SO4 concentrated The product was distilled under reduced pressure at 128-133° C.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium (9.72 g, 400 mmol), hexamethylphosphoramide (HMPA) (80 mL, 460 mmol), 1,2-dichlorobenzene (14.76 g, 100 mmol), and a catalytic amount of 12 were combined in a 500 mL round bottomed flask and heated to 70° C. with stirring. Chlorotrimethylsilane was added dropwise to the solution at 70° C. The solution was stirred for an additional 30 minutes and then heated to 100° C. for 48 h. After cooling, the reaction mixture was poured over ice and NaHCO3. The Mg and precipitate were filtered off and the filtrate was extracted with ether (3×, 200 mL). The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) and dried with Na2SO4 and concentrated. The product was distilled under reduced pressure at 128-133° C. to yield a light yellow oil (12.0426 g, 54.13%). 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 7.49 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 0.55 (s, 18H, CH3); 13C NMR (300 MHz, CDCl3) δ 145.98, 135.17, 127.76, 1.96 The solution was stirred for an additional 30 minutes heated to 100° C. for 48 h After cooling The Mg and precipitate were filtered off the filtrate was extracted with ether (3×, 200 mL) The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) dried with Na2SO4 concentrated The product was distilled under reduced pressure at 128-133° C.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Magnesium (9.72 g, 400 mmol), hexamethylphosphoramide (HMPA) (80 mL, 460 mmol), 1,2-dichlorobenzene (14.76 g, 100 mmol), and a catalytic amount of I2 were combined in a 500 mL round bottomed flask and heated to 70° C. with stirring. Chlorotrimethylsilane was added dropwise to the solution at 70° C. The solution was stirred for an additional 30 minutes and then heated to 100° C. for 48 h. After cooling, the reaction mixture was poured over ice and NaHCO3. The Mg and precipitate were filtered off and the filtrate was extracted with ether (3×, 200 mL). The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) and dried with Na2SO4 and concentrated. The product was distilled under reduced pressure at 128-133° C. to yield a light yellow oil (12.0426 g, 54.13%). 1H NMR (300 MHz, CDCl3) δ 7.85 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 7.49 (dd, 2H, J=3.4 Hz, J=5.5 Hz, ArH), 0.55 (s, 18H, CH3); 13C NMR (300 MHz, CDCl3) δ 145.98, 135.17, 127.76, 1.96 The solution was stirred for an additional 30 minutes heated to 100° C. for 48 h After cooling The Mg and precipitate were filtered off the filtrate was extracted with ether (3×, 200 mL) The organic phase was washed with water (2×, 400 mL) and brine (1×, 400 mL) dried with Na2SO4 concentrated The product was distilled under reduced pressure at 128-133° C.

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1. the reaction mixture was stirred for 2 h to stir at room temperature for 2 h Concentration of the reaction mixture gave crystals which were triturated in ether collected by filtration