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Topic: Synthesys plan. Would this work?  (Read 2439 times)

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Offline samuel

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Synthesys plan. Would this work?
« on: December 09, 2011, 07:24:10 AM »
See the picture attached

Thanks¡¡¡

Offline fledarmus

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Re: Synthesys plan. Would this work?
« Reply #1 on: December 09, 2011, 07:27:48 AM »
What happens when you add a weak acid to a strong base? Think about your grignard and methanol...

You might want a different nucleophile there.

Offline samuel

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Re: Synthesys plan. Would this work?
« Reply #2 on: December 09, 2011, 07:34:17 AM »
Oh, I'm a bit stupid. Would this work changing MeOH by MeBr or MeCl?

Offline fledarmus

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Re: Synthesys plan. Would this work?
« Reply #3 on: December 09, 2011, 07:45:00 AM »
In a formal sense, on paper, yes it would work now, and is probably satisfactory for a first-year organic class. It does have a couple of problems from a laboratory point of view that might be worth considering...

1) MeBr and MeCl are both toxic gases and are difficult to work with. In fact, the major use for methyl bromide is as an industrial fumigant to kill insects. There is a much more convenient, cheap alternative that is almost always used when you need a methyl nucleophile.

2) Chlorine free radical halogenations are not very selective - you will get a mixture of compounds mono-chlorinated at each available site, as well as dichlorinated species, and so on. You might want to consider a somewhat less reactive halogen for that step.

Offline samuel

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Re: Synthesys plan. Would this work?
« Reply #4 on: December 09, 2011, 07:53:54 AM »
Thank you. It's a theoretical exercise. Maybe Br2 would be more selective to the 3º position.
Anyway thaks for your help.

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