Gruinard reagent long questions
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What reaction conditions do you use? Because this looks like there may be several things wrong.
1) Atmosphere. You need to keep argon or nitrogen atmosphere tight to avoid reagent oxidation.
2) Heat. If you have a highly reactive radical forming? you may want to start cooling reaction on a water or water/ice bath right after it initiates.
3) Too much iodine. That's a rare one, but some people get overzealous and iodides are way too reactive sometimes. If your magnesium is fresh, iodine may not be needed at all.
4) Concentration. I've done this before- if you don't scale the amount of solvent (THF) in reaction appropriately it may get too exothermic and reagent may degrade in process.
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