Porphyrin undoubtedly represents one of the most widely studied of all known macrocyclic ring systems. Porphyrin with its multiple biological functions as well as its ability to function as an excellent metal-complexing ligand has inspired the study of a whole range of porphyrin analogs in recent years. The synthesis of a precursor 1,2-bis(1H-pyrrol-2-yl)ethane 1, leading to novel pyrrole macrocycles in ionic liquids (ILs) as a reaction media is described herein. The first approach involving six steps provided a low yield (overall 11%) of 1, whereas the one-pot approach involving bromo triflate 8 as a substrate provided 28% of 1. This modified version of pyrrole macrocycles is expected to have a specific ion-binding ability.