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Author: Subject: Phenyllithium attemt
fastbre4k
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[*] posted on 2-1-2017 at 08:52
Phenyllithium attemt


Hey,

i tried to preparate Phenyllithium.

in 150ml of Chlorobenzene was added 2g of lithium (fine strips)(from battaries) - then i started a reflux. Within 5 minutes i noticed a color change from , first light green and then going into dark yellow.

I guess that : https://en.wikipedia.org/wiki/Aryne
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PirateDocBrown
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[*] posted on 2-1-2017 at 10:31


You dropped the Li directly into the PhCl?

Next time, try a solvent. Dry Et2O or THF, for example.

Sparge your reactant/solvent with inert gas before adding the metal, and exclude atmospheric O2 from the reaction.

You will get better results with PhBr.

Also, a catalytic amount of Na metal has always helped me a bit.
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fastbre4k
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[*] posted on 2-1-2017 at 11:03


Jea - directly

mhm - next time with solvent - i guess xylene would work?

inert gas i have - N2



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draculic acid69
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[*] posted on 24-9-2018 at 05:25


So how did it go with xylene?
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S.C. Wack
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[*] posted on 24-9-2018 at 13:46


Not well I bet.

It's not an oversight that the directions (edit: e.g. OS CV2 page 517) say bromobenzene and ether (preferably with a bit of sodium) and don't say feel free to substitute with chlorobenzene and xylene.

[Edited on 24-9-2018 by S.C. Wack]




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JJay
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[*] posted on 24-9-2018 at 14:15


Phenyllithium will react with xylene, exchanging a benzylic hydrogen per methyl group for lithium. It will also react with toluene.





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