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Topic: 2,4,6-triphenylaniline  (Read 4152 times)

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Offline Schrödinger

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2,4,6-triphenylaniline
« on: June 01, 2016, 05:12:48 PM »
Has anyone here made 2,4,6-triphenyl aniline before? I tried making it using a Suzuki coupling reaction, starting from 2,4,6-tribromoaniline. Standard literature prep. Miura et al, Synthesis, 1995, pp 1419

I was supposed to get a white solid but all I get is a brownish goo. Any tips? I don't know what I'm doing wrong
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Offline kriggy

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Re: 2,4,6-triphenylaniline
« Reply #1 on: June 02, 2016, 01:26:52 AM »
Does the brownish goo contain your product?
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Offline Schrödinger

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Re: 2,4,6-triphenylaniline
« Reply #2 on: June 02, 2016, 12:03:21 PM »
I'm not sure. The proton NMR doesn't look great, but it does look like there are a few product peaks
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Offline wildfyr

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Re: 2,4,6-triphenylaniline
« Reply #3 on: June 02, 2016, 05:16:28 PM »
Quote from: Schrödinger on June 01, 2016, 05:12:48 PM

I was supposed to get a white solid but all I get is a brownish goo. Any tips? I don't know what I'm doing wrong

Rinse and repeat this phrase a few thousand times during a career
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Offline phth

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Re: 2,4,6-triphenylaniline
« Reply #4 on: June 03, 2016, 10:39:39 PM »
There could be several reasons for this.  A common problem is nanoparticle formation during cross coupling reactions.  This would lead to C-H functionalization which could be the cause.  For example, palladium(II) nanoparticles can functionalize benzene quantitatively: http://dx.doi.org/10.1016/j.molcata.2013.01.011
side products also include things such as biphenyl etc etc
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