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Topic: Sandmeyer side reactions  (Read 3252 times)

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Offline democanarchis

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Sandmeyer side reactions
« on: May 04, 2010, 02:21:52 PM »
Attempted a sandmeyer reaction today of a 1-bromo-2-amino arene. Don't appear to have any of the product, but all the starting material was consumed. The compound I obtained doesn't have an amine present, but has one more proton present, ie it isnt a 1,2 dihalo compound. It doesnt match with reference spectra for the 2-bromo or chloro. Has anyone seen electrophilic aromatic substitution of a bromo for a chloro under sandmeyer conditions, ie the 1-chloro product. Should be able to get a high res mass spec tomorrow, but would like an idea what to look for.

Offline OC pro

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Re: Sandmeyer side reactions
« Reply #1 on: May 04, 2010, 03:04:51 PM »
More detailed reaction conditions would be helpful...

Offline democanarchis

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Re: Sandmeyer side reactions
« Reply #2 on: May 04, 2010, 03:22:05 PM »
I used the conditions from this paper: dx.doi.org/10.1139/V05-026

Basically HCl/DMSO added dropwise to Ar-NH2, CuCl, KNO2 in DMSO, then poured into aq. K2CO3 (All @35 degrees C)

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