Methyl iodide → HCID 57883983, compound

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.

1. temperaturecooled in a dry ice-acetone bath under argon atmosphere
2. stirringthe mixture was stirred for 2 hours
3. stirringthe mixture was stirred at room temperature for 2 hours
4. extractionextracted with diethylether
5. washThe organic layer was washed successively with 0.5N HCl, water
6. dry with materialan aqueous saturated sodium hydrogencarbonate solution and bribe, dried over sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe resultant residue was purified by column chromatography on silica gel (Solvent; n-hexane→n-hexane/ethyl acetate=90/10)

ORD record

ord-0d7d137646474565949942a71d0a5431

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08188073B2