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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: Schrödinger on June 01, 2016, 05:12:48 PM

Title: 2,4,6-triphenylaniline
Post by: Schrödinger 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

Title: Re: 2,4,6-triphenylaniline
Post by: kriggy on June 02, 2016, 01:26:52 AM

Does the brownish goo contain your product?

Title: Re: 2,4,6-triphenylaniline
Post by: Schrödinger 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

Title: Re: 2,4,6-triphenylaniline
Post by: wildfyr 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

Title: Re: 2,4,6-triphenylaniline
Post by: phth 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