(2-(4-bromophenyl)ethynyl)triisopropylsilane

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 33.8 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 17.4 g 1-bromo-4-triisopropylsilylethynyl-benzene in 120 ml dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 10.8 g 5-bromo-2-fluoro-benzaldehyde dissolved in 30 ml of tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm up overnight to ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1). are added dropwise over 15 min The resulting solution is left in the cooling bath to warm up overnight to ambient temperature the mixture is extracted with ethyl acetate The combined organic phases are dried over sodium sulfate the solvent is removed The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 33.8 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 17.4 g 1-bromo-4-triisopropylsilylethynyl-benzene in 120 ml dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 10.8 g 5-bromo-2-fluoro-benzaldehyde dissolved in 30 ml of tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm up overnight to ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1). are added dropwise over 15 min The resulting solution is left in the cooling bath to warm up overnight to ambient temperature the mixture is extracted with ethyl acetate The combined organic phases are dried over sodium sulfate the solvent is removed The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate 4:1)

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 33.8 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 17.4 g 1-bromo-4-triisopropylsilylethynyl-benzene in 120 ml dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 10.8 g 5-bromo-2-fluoro-benzaldehyde dissolved in 30 ml of tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm up overnight to ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phase are dried over sodium sulphate, and the solvent is removed. The residue is purified through silica gel (cyclohexane/ethyl acetate 4:1). are added dropwise over 15 min The resulting solution is left in the cooling bath to warm up overnight to ambient temperature the mixture is extracted with ethyl acetate The combined organic phase are dried over sodium sulphate the solvent is removed The residue is purified through silica gel (cyclohexane/ethyl acetate 4:1)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 33.8 ml of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 17.4 g 1-bromo-4-triisopropylsilylethynyl-benzene in 120 ml dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 10.8 g 5-bromo-2-fluoro-benzaldehyde dissolved in 30 ml of tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm up overnight to ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phase are dried over sodium sulphate, and the solvent is removed. The residue is purified through silica gel (cyclohexane/ethyl acetate 4:1). are added dropwise over 15 min The resulting solution is left in the cooling bath to warm up overnight to ambient temperature the mixture is extracted with ethyl acetate The combined organic phase are dried over sodium sulphate the solvent is removed The residue is purified through silica gel (cyclohexane/ethyl acetate 4:1)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 14.8 mL of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 8.0 g 1-bromo-4-triisopropylsilylethynyl-benzene in 80 mL dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 5.1 g 3-bromo-4-methoxy-benzaldehyde dissolved in 20 mL tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm to ambient temperature overnight. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1). are added dropwise over 15 min The resulting solution is left in the cooling bath to warm to ambient temperature overnight the mixture is extracted with ethyl acetate The combined organic phases are dried over sodium sulfate the solvent is removed The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 14.8 mL of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 8.0 g 1-bromo-4-triisopropylsilylethynyl-benzene in 80 mL dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 5.1 g 3-bromo-4-methoxy-benzaldehyde dissolved in 20 mL tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm to ambient temperature overnight. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1). are added dropwise over 15 min The resulting solution is left in the cooling bath to warm to ambient temperature overnight the mixture is extracted with ethyl acetate The combined organic phases are dried over sodium sulfate the solvent is removed The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1)

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 14.8 mL of a 1.6 M solution of n-butyllithium in hexane are added dropwise under argon to a solution of 8.0 g 1-bromo-4-triisopropylsilylethynyl-benzene in 80 mL dry tetrahydrofuran chilled to −78° C. The solution is stirred for 1 h at −70° C. Then 5.1 g 3-bromo-4-methoxy-benzaldehyde dissolved in 20 mL tetrahydrofuran are added dropwise over 15 min. The resulting solution is left in the cooling bath to warm to ambient temperature overnight. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed. The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1). are added dropwise over 15 min The resulting solution is left in the cooling bath to warm to ambient temperature overnight the mixture is extracted with ethyl acetate The combined organic phases are dried over sodium sulfate the solvent is removed The residue is purified over silica gel (cyclohexane/ethyl acetate 9:1->1:1)