Thionyl Chloride → 2-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-nitro-3-(trifluoromethyl)pyridin-2-ol (9 g, 43.2 mmol) in SOCl2 (30 mL, 411 mmol) was added a catalytic amount of DMF (0.033 ml, 0.432 mmol). The mixture was stirred at 80° C. overnight. After LCMS analysis showed the starting material was consumed, the solvent was removed in vacuo. The residue was dissolved in H2O and extracted with EA. The organic layer was washed with aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and filtered. The filtrate was concentrated to give the crude product, which was purified by column chromatography (PE/EA=10/1) to yield a yellow oil of 2-chloro-5-nitro-3-(trifluoromethyl)pyridine (8.5 g, 34.7 mmol, 80% yield): 1H NMR (400 MHz, CD3OD) δ9.43 (d, J=2.8 Hz, 1H), 8.92 (d, J=2.4 Hz, 1H); ES-LCMS m/z: 225.2 (M+H).

Provenance & Evidence