Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Nick on July 31, 2007, 09:57:43 PM
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2-methyl-1,10-phenanthroline has been previously synthesized by reacting 1,10-phenanthroline with methyllithium. In my hands and in colleagues hands, this synthesis has produced very low yield and a mixture of products that is very difficult to separate.
I am actually interested in getting to 2-trichloromethyl-1,10 phen, and I have another idea that may not require going through the 2-methyl-1,10-phen. The sythesis of 2-cyano-1,10-phen has been reported in good yield (Organometallics 2006, 25, 666). The authors hydrolyzed the cyano group, reacted the acid with thionyl chloride/methanol to give the methyl ester, and reduced to the alcohol with sodium borohydride. I want to tosylate the alcohol and react the tosylated alcohol with N-chlorosuccinimide to give 2-trichloromethyl-1,10-phen.
Does this sound feasible? Can anyone propose a simpler route to either 2-methyl-1,10-phen or 2-trichloromethyl-1,10-phen?