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Topic: effect of trifluoromethyl group on reactivity of pimary amine  (Read 2267 times)

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Offline kevalb56

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effect of trifluoromethyl group on reactivity of pimary amine
« on: January 29, 2015, 08:36:30 AM »
hello sir,
   I try to couple primary amine (ortho to -CF3 group)with aliphatic chloro in sodium hydride(solvent:-Toluene overnight reflux),(DMF overnight heating).but in both solvents reaction can't moved more than 20%.so please give me advice fast what can I do to complete reaction?
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Offline TheUnassuming

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Re: effect of trifluoromethyl group on reactivity of pimary amine
« Reply #1 on: January 29, 2015, 09:36:29 AM »
Primary amine=benzylamine?
How are you monitoring the reaction?
I wouldn't use DMF, especially if you are heating it up since DMF has the tendency to decompose when heated.
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When in doubt, avoid the Stille coupling.
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