Methyl iodide → HCID 57883983, compound

Participants

Reaction Steps

To a solution of diisopropylamine (1.42 mL) in tetrahydrofuran (15 mL) was added dropwise 1.6 M n-butyl lithium-n-hexane solution (6.37 mL) cooled in a dry ice-acetone bath under argon atmosphere, and the mixture was stirred at the same temperature for 20 minutes. Thereto was added dropwise a solution of 2-chloro-6-(trifluoromethyl)pyridine (1.81 g) in tetrahydrofuran (5 mL), and the mixture was stirred for 2 hours. To the reaction mixture was added methyl iodide (0.69 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was diluted with water and extracted with diethylether. The organic layer was washed successively with 0.5N HCl, water, an aqueous saturated sodium hydrogencarbonate solution and bribe, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent; n-hexane→n-hexane/ethyl acetate=90/10) to give 2-chloro-3-methyl-6-(trifluoromethyl)pyridine (0.90 g) as a yellow powder.

Provenance & Evidence