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Ketone bromination problems

Ziconotide
in Organic Chemistry

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I am doing some scientific research on thiazole chemistry. I have to brominate 1-(2-(pyridin-4-yl)thiazol-5-yl)ethanone to obtain the bromoketone. I've tried this with elemental bromine in carbon tetrachloride(stirring, reflux) and obtained a red powder after vacuum filtration . The problem is that this molecule has to 2 aromatic N atoms and the bromine is actually incorporated into the molecule. The 1HNMR spectra shows that there has no bromination occured. I have tried to brominate it with NBS/CCl4 + 2 drops HCl conc under reflux. TLC shows that the bromination is incomplete. I have to try some other systems like NBS/MeCN or NBS/DMF with an appropriate catalyst. TsOH might be a very good idea but the problem is that can form salt with my haloketone complicating isolation.

 

So : Which is the best method to halogenate this molecule and how to isolate the product (in base form not pyridinum salt) ?

 

 

Has anyone brominated a Pyridinium ketone compund ?

 

 

 

 

Thank you.

 

 

 

 

Smith

Edited by Ziconotide

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