I did the bromination reaction with NBS as shown in the attached file. After purifying my product by flash chromatography the nmr 1H spectrum shows presence of succinimide including my product, wich means that succinimide coelutes with my product during the purification. Does somebody knows a way to get ride of the succinimide in that situation?
Thank you.
Mathieu
Hi,
Ok this may seem pretty obvious, but have you tried running an hplc analysis on your product after the flash chromatography? I think your best option is to use reverse phase Prep or Semi-prep HPLC. I extremely doubt that succinimide will still co-elute on HPLC.
Another way will be an acid base extraction, but you have to be careful of product decomposition. you have a labile ester that may be hydrolyzed under acidic conditions.
Succinimide is Insoluble in: Et2O, hexane, CCl4
Slightly soluble: Water, AcOH
Try dry flash and ad to your eluent 1-5% of Et3N (or NH3/MeOH), your acid will travel realy slow, as a salt, but succinimide will eluate much faster (much weaker acid)
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