Lithium diisopropylamide (LDA)-mediated ortholithiations of 2,6-difluoropyridine in tetrahydrofuran at -78°C has been studied using a combination of IR and NMR spectroscopic and computational methods. Polycondensation of bistrimethylsilyl derivatives of various diphenols with 2,6-difluoropyridine in N-methylpyrrolidone in the presence of K2CO3 has been investigated.