Triphenylphosphine → 4-(3,3-Dimethylbut-1-yn-1-yl)benzaldehyde

Participants

Reaction Steps

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%).

Provenance & Evidence