3-bromo-2-(chloromethyl)pyridine

A solution of cis-4-(2, 3, 6-trifluorophenyl)cyclohexanol (3.66 g) in THF (100 ml)was cooled to 0C, 60% sodium hydride (1.272 g) was added, and the mixture wasstirred under a calcium chloride tube dry atmosphere at room temperature for 10 min.To the reaction mixture was added A solution of cis-4-(3-fluorophenyl)cyclohexanol (1.0 g) in THF (20 ml) was cooledto 0C, 60% sodium hydride (0.412 g) was added, and the mixture was stirred under acalcium chloride tube dry atmosphere for 1 hr. To the reaction mixture was addedA solution of cis-4-(2, 6-difluorophenyl)cyclohexanol (2.69 g) in THF (60 ml) wascooled to 0C, 60% sodium hydride (1.014 g) was added, and the mixture was stirredunder a calcium chloride tube dry atmosphere for 2 hr. To the reaction mixture wasadded A solution of cis-4-(2, 5-difluorophenyl)cyclohexanol (2.85 g) in THF (60 ml) wascooled to 0C, 60% sodium hydride (1.074 g) was added, and the mixture was stirredunder a calcium chloride tube dry atmosphere at room temperature for 2 hr. To thereaction mixture was added To a solution of cis-4-(2-methoxyphenyl)cyclohexanol (889 mg) in THF (20 ml) wasadded 60% sodium hydride (345 mg) at 0C, and the mixture was stirred at under anitrogen atmosphere at room temperature for 2 hr. To the reaction mixture was added...oxymethylpyridine, 3-bromo-2-hydroxymethylpyridine and 4-bromo-5-hydroxymethylimidazole may be converted into 3-chloro-2-chloromethylpyridine,