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Natural Science Forum / Chemistry / Organic Synthesis / February 2006



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How do I synthesize ....

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Pierre27_9 - 02 Feb 2006 09:05 GMT
hello,
does anybody have any idea how could I synthesize compounds such as:
- 4-fluoro-4'-thiol tolane
- 4-(4'-thiolphenyl ethynyl) toluene,
- 4-(4'-thiolphenyl ethynyl) acetophenone
- 4-(4'-thiolphenyl ethynyl) benzoic acid
Thank you very much ;)
Sincerely,
Pierre
Andrew Tweddle - 06 Feb 2006 09:25 GMT
> hello,
> does anybody have any idea how could I synthesize compounds such as:
[quoted text clipped - 5 lines]
> Sincerely,
> Pierre

This might get you started

"The Synthesis of Some Tertiary Amine Derivatives of Mixed Phenyl Alkyl
Sulfides"

J.A.C.S. 1952

I see, compounds of pharmacological interest ;)

Andrew
Andrew Tweddle - 06 Feb 2006 09:26 GMT
> hello,
> does anybody have any idea how could I synthesize compounds such as:
[quoted text clipped - 5 lines]
> Sincerely,
> Pierre

Your probably making life unduly difficult on yourself.
I did a quick search and a little thinking. My suggestions are:

Post this to sci.chem ,this group is about dead!

If you know the molecules you are dealing with then a search on
Beilstein /Discoverygate may be the go.

The names seem not to be in very common usage.

You can use a service such as

chemrefer.com

and

http://www.webreactions.net/search.html

to progress your search.

Webreactions even if it doesn't find anything useful, at least allows
you to draw the molecule and clarify your thinking on how to put it
together.

Google Scholar can be very useful for tracking down obscure reactions
from J.A.C.S.

Also the USPTO. Do a search for the inventor or assignee of the
compound. Pre 1975 searchs are however virtually impossible.
FreePatensonline allow you to download the answers in PDF and not TIFF
which is just marvelous.

Andrew
Gabriel Tojo - 07 Feb 2006 08:52 GMT
I would try in all compounds a Sonogashira coupling using a
p-substituted phenylacetylene on one side and S-protected
p-iodothiophenol on the other side.

Best regards.

Gabriel Tojo

Consultant in Organic Synthesis
 
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