Over the summer, a project was pursued to generate a novel solid-phase material to transform alcohols to alkyl halides.  Our plan was the bind the solid-state transforming agent to Merrifield Peptide Resin to create a material which could be regenerated as a transforming agent.  A Friedel-Crafts alkylation was used to bind xanthone to Merrifield peptide resin. Before proceeding with the alkylation, the polymer was washed with different organic solvents, including dichloromethane and ethyl acetate, until the polymer stopped losing mass after consecutive washes. The polymer and xanthone were bound together and results were verified by solid state IR analysis. The xanthone-bound polymer was reacted with thionyl chloride and a primary alcohol to transform the alcohol into an alkyl halide. <br/>

Development of a polymer-backed, regenerating chlorinating agent

255th National Meeting (2018)

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