I need to synthesize 4-iodoresorcinol (a).
This should be simple, but it hasn't been. My first inclination was to simply iodinate resorcinol (b), but I've never done an iodination before. I have only performed chloro and bromo halogenations previously, and since I wanted to maximize yield, I didn't want to deal with the diiodo moiety.
So, I decided to use a procedure that has worked for me in the past (with bromination), using 2,4-dihydroxybenzoic acid (c). I used Iodine monochloride (1 equivalent), quenched, and decarboxylated. But either the iodination failed, or something went wrong during decarboxylation.
Any ideas?
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