Azobisisobutyronitrile → 4-Bromocrotonic acid 2,2,2-trichloroethyl ester

Participants

Reaction Steps

The bromination reaction takes place in carbon tetrachloride with N-bromosuccinimide and AIBN as radical former. For this purpose, an equimolar amount of ester (i) and 0.45 mole N-bromosuccinimide are mixed with 300 ml. carbon tetrachloride and a spatula tip of AIBN added thereto. The reaction mixture is heated under reflux for 4 hours, subsequently allowed to cool and the precipitated succinimide (0.41 mole; 92% of theory) is filtered off. After distilling off the solvent in a vacuum, the residue is purified by column chromatography using PE/PE (25:1 v/v) as elution agent. The end product obtained is a yellow oil. The yield of 75% of theory. C6H6O2BrCl3 (296.3752 g./mole).

Provenance & Evidence