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Topic: Guidance for Synthesis reaction of a sulfanyl  (Read 3411 times)

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Offline google1

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Guidance for Synthesis reaction of a sulfanyl
« on: December 02, 2010, 08:23:21 PM »
Okay, attached is the bromo-compound that is the starting compound in the synthesis of sulfanyl compound.  Any advice on this reaction would be very helpful.  I wrote out my own idea of what it might be but did not want to draw it out on ACD chem sketch.  

Offline Cesium-137

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Re: Guidance for Synthesis reaction of a sulfanyl
« Reply #1 on: December 03, 2010, 01:52:54 AM »
This is what I would try. Never actually done this, so no promises. The only problem I see is the formation of the alkene... If the methyl protons (not part of the t-bu part) are acidic enough due to the Br, a strong non-nucleophilic base should cause elimination to form the alkene. I like NaH because the deprotonation is irreversible and would go to completion. For deprotonation of the methylthiol, a non-nucleophilic base protects from unwanted addition to the chlorinated carbon. Its possible that there is a much better way to do this, but it might be worth a try! Hope it helps!

Offline google1

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Re: Guidance for Synthesis reaction of a sulfanyl
« Reply #2 on: December 03, 2010, 09:57:11 AM »
I forgot to note that the reaction can be done in 4 steps or less. 

Offline Cesium-137

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Re: Guidance for Synthesis reaction of a sulfanyl
« Reply #3 on: December 03, 2010, 11:23:58 AM »
So you already know how to run it? Maybe I misunderstood what you were asking for?

Offline google1

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Re: Guidance for Synthesis reaction of a sulfanyl
« Reply #4 on: December 03, 2010, 11:31:24 AM »
No.  We were asked for study sessions to be able to write these reactions in 4 steps.   This is one of those reactions. 

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