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Author: Subject: arylation of 2-methyl pryridine
rotwang
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[*] posted on 9-7-2006 at 17:49
arylation of 2-methyl pryridine


2-methyl pyridine (alpha picoline) loses a proton from the 2 methyl group and forms a stabilised anion when treated with sodamide or other strong base.
this anion can then react with an alkyl halide to give an 2-alkyl pyridine with an extended carbon chain.

has anyone come across a reaction in their travels where an aryl diazonium salt or a aryl halide or sulphonic acid is reacted with the anion generated from 2-methyl pyridine? In theory this would generate a 2-benzyl pyridine. would appreciate any help

BTW I know that benzyl pyridines are easy to synthesise from pyridine and benzyl lithium, its just a little more complex than that.

-R
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