Iodination of 3,5-Dichloroanisole Using Silver Salts

Fan, Alex (2017) Iodination of 3,5-Dichloroanisole Using Silver Salts. Undergraduate thesis, under the direction of Daniell Mattern from Chemistry and Biochemistry, University of Mississippi.

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Abstract

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.

Item Type: Thesis (Undergraduate)
Creators: Fan, Alex
Student's Degree Program(s): B.S. Pharmaceutical Sciences
Thesis Advisor: Daniell Mattern
Thesis Advisor's Department: Chemistry and Biochemistry
Institution: University of Mississippi
Subjects: Q Science > QD Chemistry
Depositing User: Alex Fan
Date Deposited: 11 May 2017 16:13
Last Modified: 11 May 2017 16:13
URI: http://thesis.honors.olemiss.edu/id/eprint/796

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