反应详情

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%).

1. customis thoroughly purged with nitrogen
2. temperatureheated to 100° in a sealed tube under nitrogen for 2 hr
3. temperatureThe mixture is cooled
4. customthe precipitated triethylamine hydrobromide is removed by filtration
5. concentrationThe filtrate is concentrated
6. dissolutionthe residue dissolved in 3:1 dichloromethane-hexane
7. filtrationfiltered through a 2-cm pad of silica gel
8. concentrationThe filtrate is concentrated
9. distillationvacuum-distilled