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P-DCB from DI chloro benzene

Started by Vibrating_Lights, June 06, 2003, 09:11:00 AM

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Vibrating_Lights

Can one take P dichlorobenzene and react it with MeCN to give P Dicyanobenzene.  ??


raffike

MeCN won't probably work but alkalimetal cyanides should.


Pimpo

Alkali cyanides generally don't convert aryl halides to nitriles, even activated ones. Anhydrous CuCN does react at 200°C. Look at Organic Syntheses, CV 3, 212 (9-CYANOPHENANTHRENE) and Organic Syntheses, CV 3, 631 (a-NAPHTHONITRILE). Note that heavier halogens generally react better.


Vibrating_Lights

Is ther a more common name for  Dicyanobenzene


Rhodium


Aurelius

And why was it misinforming? An explanation would be appreciated.

Pimpo

Hey Aurelius, dunno who rated your post  ;) , but the reason is the following: diazonium ions are formed from aromatic AMINES and nitrous acid, not from aromatic HALIDES. Your idea should work, but you'd have to tetrazotize (i.e. diazotize twice) p-phenylenediamine.

Aurelius

I think I need more sleep.  That's two very obvious misses I've made recently.