Carbon Tetrachloride → 5-(Chloromethyl)-2-norbornene

Participants

Reaction Steps

A mixture of triphenylphosphine (20.98 g, 0.08 mol) and bicyclo[2.2.1]hept-5-ene-2-methanol (5.0 g, 0.0403 mol) in dry carbon tetrachloride (31.5 ml) was stirred and heated at 60° for 6 h. After cooling, the reaction mixture was filtered, and the filtrate was evaporated under reduced pressure to afford a semi-crystalline mass, which was triturated with n-pentane (100 ml). The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to afford a yellow oil. Distillation of the oil afforded 5-chloromethylbicyclo[2.2.1]hept-2-ene as a colourless oil, b.p. 70°-72°/24 mm Hg.

Provenance & Evidence