Dimethylformamide → [6-(Trifluoromethyl)pyridin-2-yl]methanol

Temperature

-78 °C

A solution containing 2.00 g of 2-bromo-6-trifluoromethylpyridine dissolved in 50 ml of toluene was cooled to −78° C. followed by dropping in 4.0 ml of n-butyllithium (2.77 mol/L) and stirring for 10 minutes at −78° C. 0.96 g of N,N-dimethylformamide were dropped therein followed by further stirring for 10 minutes at −78° C. following completion of the reaction. 0.67 g of sodium borohydride and 5 ml of methanol were added to the resulting reaction mixture followed by heating to room temperature and stirring for 1 hour at room temperature. Following completion of the reaction, aqueous ammonium chloride solution was added to the reaction liquid followed by extraction with ethyl acetate. The ethyl acetate layer was dried by addition of anhydrous magnesium sulfate followed by filtering and distilling off the solvent from the filtrate under reduced pressure to obtain 1.70 g of a crude product in the form of (6-trifluoromethylpyridin-2-yl) methanol.

1. stirringby further stirring for 10 minutes at −78° C.
2. customcompletion of the reaction
3. temperatureby heating to room temperature
4. stirringstirring for 1 hour at room temperature
5. additionwas added to the reaction liquid
6. extractionfollowed by extraction with ethyl acetate
7. dry with materialThe ethyl acetate layer was dried by addition of anhydrous magnesium sulfate
8. filtrationby filtering
9. distillationdistilling off the solvent from the filtrate under reduced pressure

ORD record

ord-363ac810671f4591b024c3e85bca7053

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268755B2