Acetic Acid → 2-chloro-6-(trifluoroMethyl)pyridin-3-ol

Temperature

0 °C

A solution of 6-(trifluoromethyl)pyridine-3-ol (7 g, 40 mmol) and sodium carbonate (4.5 g, 4.2 mmol) in water (200 mL) was cooled in an ice bath. 0.7N Sodium hypochlorite solution (63.9 mL, 4.29 mmol) was added portionwise over 30 minutes, and the reaction stirred at 0° C. for 2 hours. The reaction mixture was acidified using acetic acid, and extracted into EtOAc (3×50 mL). The combined organics were washed with brine (2×50 mL), dried (MgSO4), filtered and concentrated. The product was purified by flash chromatography (0 to 25% EtOAc in hexanes) giving the title compound (1.6 g, 20%) as a solid. 1H NMR (400 MHz; CDCl3) δ 7.61 (1H, d), 7.45 (1H, d), 5.83 (1H, s).

1. extractionextracted into EtOAc (3×50 mL)
2. washThe combined organics were washed with brine (2×50 mL)
3. dry with materialdried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe product was purified by flash chromatography (0 to 25% EtOAc in hexanes)

ORD record

ord-b19563cf85ee4e9580838aa9542267c2

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153651B2