Honors Theses

Date of Award


Document Type

Undergraduate Thesis


Chemistry and Biochemistry

First Advisor

Daniell Mattern

Relational Format



A paper published by Joshi et al. showed lower than expected yields in mono- and di-iodination of 3,5-dichloroanisole in dichloromethane using silver salts. One possibility for this could be that the starting material was being tri-iodinated and precipitating out of the solution. We used similar reaction conditions in attempts to prepare and isolate triiodinated product, but attempts of recrystallization from ethanol, DMSO, and 2- methoxyethanol showed no signs of it. Removal of silver iodide from the solids formed during the reaction using aqueous potassium iodide resulted in complete dissolution of the entire crude product, suggesting no organic product as well. This reaction was then combined with the concept of a solvent-less reaction based on a paper published by Bose et al. involving electrophilic aromatic halogenation using a ball milling machine. Variation of reagent equivalents, heat, and time have shown various percent compositions of the products 3,5-dichloro-2-iodoanisole and 3,5-dichloro-2,6-diiodoanisole. Unfortunately, no attempts show any evidence of the tri-iodinated product.

Included in

Chemistry Commons



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