Sciencemadness Discussion Board

whats the best reagent to do monochlorination

smartgene - 25-8-2016 at 15:15

what is the best reagent to do a monochlorination on the alpha position of a ketone with minimum side reaction like di tri

Dany - 25-8-2016 at 15:44

Treating of a ketone with lithium diisopropylamide (LDA) followed by p-toluenesulfonyl chloride (p-TsCl) gives α-chloroketone. This method has been described by Brummond & Gesenberg (see attached file and references therein).

Dany.

Attachment: a-Chlorination of Ketones.pdf (19kB)
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[Edited on 25-8-2016 by Dany]

smartgene - 25-8-2016 at 16:57

Im looking for a reagent that can easily prepared

AvBaeyer - 25-8-2016 at 19:28

This can be easily accomplished using TCCA with an acid catalyst (chloroketone) or with 1,3-dibromo-5,5-dimethylhydantoin (non-cholorine pool treatment) to give the bromoketone again with an acid catalyst. There are several accesible free references on this if you do a google/google scholar search.

AvB

PHILOU Zrealone - 26-8-2016 at 09:35

Cl2/HCl is also sometimes used like for chloropropanone see "The War Gases: Chemistry and Analysis" book into the Library.