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In a detailed study of conditions for monolithiation with n-BuLi, it was found that coordinating solvents, e.g. ether, and high concentrations favor 5-substitution, while non-coordinating sovents, e.g. toluene, and lower concentrations favor 2-substitution. At -78o C in toluene, good yields of various 2-substituted 5-bromopyridines were obtained: Tetrahedron Lett., 41, 335 (2000).