Re: ORGLIST:synthetic route of 2-(2,4-difluorophenyl)pyridine

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From: Maringanti Krishnamacharyulu (maringanti9$##$yahoo.com)
Date: Tue Mar 11 2003 - 10:40:16 EST

Hi!

The best way is to start from 2-chloropyridine. Try to generate a Grignard from 2-bromo-1,3-difluorobenzene. (you could try a Magnesium exchange reaction.. look for the exact procedure). Treat, a solution of 2-chloropyridine, in THF and N-Methyl Morpholine (3:1) with Fe(acac) (10 mol%). Cool it to -40, add the Grignard reagent, and stirr it till the reaction is complete (about 10-30 minutes!).

Usual work up, followd by kugelror distillation should furnish the desired compound

Good Luck!

Krishna

P.S. Dont attempt to prepare an aryl lithium from fluoroaromatic, since, you would end up with benzyne, and consequently many complex products!

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