Influence of scale, stoichiometry and temperature on the synthesis of 2,8-dihalo analogues of Tröger's base from the corresponding anilines and paraformaldehyde

Abstract

The yields of 2,8-dihalo analogues of Tröger's base in the condensation between 4-haloanilines and paraformaldehyde was found to be highly sensitive to the crucial reaction parameters of scale, stoichiometry and temperature. The reaction conditions were optimized allowing for the semi-large scale synthesis of the 2,8-diiodo- (2) and 2,8-dibromo- (3) analogues, respectively.