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Topic: Reactions with Aniline  (Read 3960 times)

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Offline mbckenny

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Reactions with Aniline
« on: May 12, 2012, 10:20:25 AM »
Hi,

I am going over some reactions with aniline and have a few queries.

1) If I want to add a bromine para to the NH2 I have the following steps written down... i) add ethanoic anhydride, ii) add Br2 and HoAc, iii) add HCl, EtOH, H2O.
    For the second step, does it have to be Br2 with HoAc or can I use Br2 and FeBr3?

2) If I am trying to replace the NH2 with a Br, I have the following steps... i) NaNO2, HCl, ii) CuBr
    For the second step can I not just use Br2?

Cheers,
Mike

Offline Schrödinger

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Re: Reactions with Aniline
« Reply #1 on: May 13, 2012, 10:21:11 AM »
1) Br2/FeBr3 should be fine, I guess.. Since the LP on N is 'de-natured' by protecting the NH2 with an acetyl group, I guess the Lewis acid shouldn't pose any threat.

2) The Sanmeyer reaction is catalyzed by the Cu+ ion. That's why it is more effective than simply adding a molecule of Bromine
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Offline mbckenny

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Re: Reactions with Aniline
« Reply #2 on: May 16, 2012, 07:44:41 AM »
Cheers

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