[Nick]

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?