Toluene → 2-chlorobicyclo[2.2.1]hept-5-ene-2-carbonitrile

Participants

Reaction Steps

To a solution of 2-chloroacrylonitrile (50.0 g, 571 mmol) in toluene (150 ml) was slowly added cyclopentadiene (37.7 g, 571 mmol). The reaction was stirred for 60 h at ambient temperature under a nitrogen atmosphere. The reaction was then concentrated by rotary evaporation to remove the majority of the toluene. The compound was purified by vacuum distillation (100-150° C., 15 mm Hg) to afford the nitrile as a white solid (49.7 g, 56.5%).

Provenance & Evidence