Dimethylformamide → 3-(Chloromethyl)-2-methyl-6-(trifluoromethyl)pyridine

To a solution of (2-methyl-6-(trifluoromethyl)pyridin-3-yl)methanol (14.5 g, 71 mmol) in 100 mL CH2Cl2 at room temperature under argon was added SOCl2 (16.8 g, 142 mmol), followed by about 1.5 mL DMF, which was added to re-dissolve the rapidly formed, precipitating hydrochloride salt of the starting material. The resulting reaction mixture was stirred for 16 h. HPLC/MS analysis indicated that the reaction was complete. Solvent was evaporated under vacuum. The resulting residue was dissolved in 200 mL Et2O, and the resulting solution was washed with 10% aqueous sodium carbonate solution (100 mL), then saturated aqueous NaCl (100 mL). The organic phase was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to obtain 13.7 g of the title compound as a tan oil, which was greater than 98% pure. HPLC/MS: retention time=2.9 min, [M+H]30 =210.

1. additionwas added
2. dissolutionto re-dissolve the
3. customrapidly formed
4. customprecipitating hydrochloride salt of the starting material
5. customThe resulting reaction mixture
6. customSolvent was evaporated under vacuum
7. dissolutionThe resulting residue was dissolved in 200 mL Et2O
8. washthe resulting solution was washed with 10% aqueous sodium carbonate solution (100 mL)
9. dry with materialThe organic phase was dried over anhydrous sodium sulfate
10. filtrationfiltered
11. concentrationThe filtrate was concentrated under vacuum

ORD-Eintrag

ord-33eaa5365fb94577a865ba2c68932c80

Quelldatensatz

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07452892B2