4-(3,3-dimethylbut-1-ynyl)benzaldehyde

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

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

Procedure: A mixture of 4-bromobenzaldehyde (3.7 g), triphenylphosphine (0.32 g), palladium(II) acetate (135 mg), and 3,3-dimethyl-1-butyne (4 ml) in triethylamine (20 ml) is thoroughly purged with nitrogen, then heated to 100° in a sealed tube under nitrogen for 2 hr. The mixture is cooled, and the precipitated triethylamine hydrobromide is removed by filtration. The filtrate is concentrated, and the residue dissolved in 3:1 dichloromethane-hexane and filtered through a 2-cm pad of silica gel. The filtrate is concentrated and vacuum-distilled to provide 4-(3,3-dimethyl-1-butynyl)benzaldehyde as a pale yellow solid (3.25 g, 86%). is thoroughly purged with nitrogen heated to 100° in a sealed tube under nitrogen for 2 hr The mixture is cooled the precipitated triethylamine hydrobromide is removed by filtration The filtrate is concentrated the residue dissolved in 3:1 dichloromethane-hexane filtered through a 2-cm pad of silica gel The filtrate is concentrated vacuum-distilled

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

Procedure: A mixture of 4-bromobenzaldehyde (3.7 g), triphenylphosphine (0.32 g), palladium(II) acetate (135 mg), and 3,3-dimethyl-1-butyne (4 ml) in triethylamine (20 ml) is thoroughly purged with nitrogen, then heated to 100° in a sealed tube under nitrogen for 2 hr. The mixture is cooled, and the precipitated triethylamine hydrobromide is removed by filtration. The filtrate is concentrated, and the residue dissolved in 3:1 dichloromethane-hexane and filtered through a 2-cm pad of silica gel. The filtrate is concentrated and vacuum-distilled to provide 4-(3,3-dimethyl-1-butynyl)benzaldehyde as a pale yellow solid (3.25 g, 86%). is thoroughly purged with nitrogen heated to 100° in a sealed tube under nitrogen for 2 hr The mixture is cooled the precipitated triethylamine hydrobromide is removed by filtration The filtrate is concentrated the residue dissolved in 3:1 dichloromethane-hexane filtered through a 2-cm pad of silica gel The filtrate is concentrated vacuum-distilled

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

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

Procedure: A mixture of 4-bromobenzaldehyde (3.7 g), triphenylphosphine (0.32 g), palladium(II) acetate (135 mg), and 3,3-dimethyl-1-butyne (4 ml) in triethylamine (20 ml) is thoroughly purged with nitrogen, then heated to 100° in a sealed tube under nitrogen for 2 hr. The mixture is cooled, and the precipitated triethylamine hydrobromide is removed by filtration. The filtrate is concentrated, and the residue dissolved in 3:1 dichloromethane-hexane and filtered through a 2-cm pad of silica gel. The filtrate is concentrated and vacuum-distilled to provide 4-(3,3-dimethyl-1-butynyl)benzaldehyde as a pale yellow solid (3.25 g, 86%). is thoroughly purged with nitrogen heated to 100° in a sealed tube under nitrogen for 2 hr The mixture is cooled the precipitated triethylamine hydrobromide is removed by filtration The filtrate is concentrated the residue dissolved in 3:1 dichloromethane-hexane filtered through a 2-cm pad of silica gel The filtrate is concentrated vacuum-distilled

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