[ibeza4]

aka: isopropylphenylacetylene

I have an idea how to get this, but it may be wrong or there may be an easier way to get to the product.  The guidelines are: may only use benzene, acohols, alkyl halides with 3 carbons or less, and inorganic reagents can be used.  I have a feeling there is an easier way since we don't even get into dehydrogenations and Sonogashira couplings in orgo2.

This is what I have:
1) Benzene + CH3CH2CL ->ALCL3-> to give ethylbenzene
2) dyhydrogenation performed to give ethenylbenzene
3) addition of Br2 to give (1,2-Dibromoethyl)-benzene
4) NaNH2 in lquid ammonia to give phenyl acetylene
5) Sonogashira Coupling performed with 2-bromopropane to give the final product

Thank you for any help that anyone can give.

[lutesium]

Yes that synthesis is possible but why don't you simply make a Sonogashira Coupling between Ph-X and
3-methylbut-1-yne?


Lutesium...

[ibeza4]

Thanks for the response, Lutesium.
That would probably be the best thing to do in reality, but my professor wants us to try to figure out with only the things we have covered.  We haven't even covered the Sono coupling, so I'll have to see what she says about that.

[lutesium]

Which route do you think for dehydrogenation? Because AFAIK its hard to dehydrogenate EthylBenzene to Styrene.


Lutesium...