2-Bromobenzaldehyde → 2-(1-Tridecynyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Palladium acetate (96 mg) was added to a deaerated mixture of 2-bromobenzaldehyde (7.40 g, 40 mmol), 1-tridecyne (12.2 g, 68 mmol) and triphenylphosphine (320 mg) in dry triethylamine (160 ml) and the mixture was stirred at 105° C. under a nitrogen atmosphere overnight. After cooling, the precipitated triethylamine hydrobromide was filtered off and the filtrate was evaporated to a crude red oil. Chromatography on silica gel eluting with dichloromethane:petroleum ether [bp 60°-80° C.](1:1) afforded 7.12 g (63%) of the title compound of bp0.05 212° C. (Kugelrohr), M+ 284.2141 (C20H28O requires; 284.2140).

Provenance & Evidence