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Topic: Is this process going to work? (SnAr, Nitrogen involved)  (Read 12788 times)

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Offline Dan

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Re: Is this process going to work? (SnAr, Nitrogen involved)
« Reply #15 on: April 05, 2013, 03:20:47 AM »
Cl-Ar-CN ---(NaOH)---> CN-Ar-Cl

I really doubt this will work - I don't think CN is electron withdrawing enough to facilitate the addition of hydroxide - this mechanism usually requires nitro groups or multiple electron withdrawing groups. Also, you will probably get nitrile hydrolysis with NaOH before you get SNAr. Maybe see where you get with p-chloronitrobenzene.


On a side note, does anyone know if the Vilsmeier-Haak reaction works on unprotected anilines?
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Offline opsomath

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Re: Is this process going to work? (SnAr, Nitrogen involved)
« Reply #16 on: April 05, 2013, 03:57:27 PM »
Considering that N-methylformanilide is the CHO donor of choice in Vilsmeier-Haack, I'm guessing that if you did it on an unprotected aniline you'd wind up formylating the nitrogen.

Offline orgopete

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Re: Is this process going to work? (SnAr, Nitrogen involved)
« Reply #17 on: April 05, 2013, 04:11:16 PM »
Just to keep this from languishing, I'd do something like this. First synthesis an o/p directing group, for example a methyl or a hydroxy group. Nitration should give an o/p-mixture from which the para isomer can be isolated. If this were done on the phenol, then reduction, diazotization, and cyanide can give the desired product. If from toluene, he nitro group can be converted to the phenol, oxidation of the methyl group to a carboxylic acid, conversion to an amide and dehydration to the nitrile would also give the product.
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