Date of Award
Bachelor of Science
James C. Adrian Jr.
The Ullmann ether synthesis is a reaction that couples aryl halides to aliphatic alcohols. It works best with aryl iodides because the aryl bromides are much less reactive, and aryl chlorides are even more so. A Finkelstein type halogen exchange reaction has been shown to effectively substitute iodide for bromide on aryl bromides with high yields. The goal of this project is to develop a one pot halogen exchange, Ullmann coupling reaction to allow for aryl bromides to be coupled successfully to aliphatic alcohols. This is feasible because the reaction conditions of the two reactions are so similar. Several condition variables were tested to attempt to achieve the highest amount of conversion possible. Different solvent systems, such as pairing methanol with dioxane, dimethylformamide, toluene, and N-methyl-2-pyrrolidone, were tested as well as a number of ethylenediamine based ligands. The conditions that were best suited to produce the ether products used ethylenediamine as a ligand with a copper iodide catalyst in neat methanol. This data can be seen in further detail in Table 8, entry 6.
Campedelli, Antonio, "Synthesis of Alkyl Aryl Ethers Using a Halogen Exchange Coupled to an Ullmann Etherification" (2020). Honors Theses. 2376.