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Thanks for your answer! I tried this paper you sent too, but the yied is very low!  I just want to prepare 4-chloropyridine, which way isn't important! I already found the synthesis of 4-chloropyridine from 4-pyridylpyridinium dichloride but my problem is that i can't prepare 4-pyridylpyridinium dichloride.

You can start from 4-hydroxypyridine which is comercially available and then with PCl5 (phosphorous pentachloride) or PCl3 you can get 4-chloropyridine in high yield.

Thank all! I'm trying

Thanks to all researchers these informations were useful to me also

4-Chloropyridine is not stable and reacts with itself, which maybe why your yield is low, the compound is only stable as it's hydrochloride salt. This is commercially available [CAS 7379-35-3] and is cheap to buy.

try pyridine reacts with SOCl2 in AcOEt 400C ~ 750C

• 4-Nitropyridine n Oxide reacts with PCl3 to cause Nitro replacement by Cl atom and deoxygenation. Anyway, this substance is unstable if not in hydrochloride form.

You can do chlorination of 4-hydroxypyridine with POCL3 and get 4-chloropyridine and isolate it as hydrochloride salt. 4-chloropyridine HCL is commercially available from Sigma - Aldrich. You can follow the link: http://www.sigmaaldrich.com/catalog/product/aldrich/c70223?lang=en®ion=IN

 33 synthesis routes and 33 suppliers in link  - must-have site in browser Favorites for real chemists

http://www.molbase.com/en/synthesis_626-61-9-moldata-226191.html#tabs

Thank you very much!

Well, Richard Bryan has provided some real world answer. I would say if you need the product rather than the exercise of making it, just follow his advice.

I have the same problem with the low yield could you help us to improve the yield as soon as possible