Reaction #43322

Reaction equation

Potassium carbonate

sodium chlorodifluoroacetate

DMF

2-bromo-5-hydroxypyridine

→

title compound

Yield 43.0%

2-bromo-5-difluoromethoxypyridine

Yield 43.0%

Solvents

ether

Conditions

Workup

1. 1
   OtherThe reaction liquid
2. 2
   Temperaturewas cooled to room temperature
3. 3
   Washwashed with water
4. 4
   Dryingdried over anhydrous magnesium sulfate
5. 5
   ConcentrationConcentrating the solvent under reduced pressure
6. 6
   Otherthe resulting residue was purified on silica gel column chromatography (C-300; hexane:ethyl acetate=100:1-100:2)

Procedure

Potassium carbonate (2.4 g, 17.3 mmols) and sodium chlorodifluoroacetate (4.2 g, 27.5 mmols) were added to a DMF (20 mL) solution of 2-bromo-5-hydroxypyridine (2.4 g, 13.8 mmols) and stirred overnight at 80° C. The reaction liquid was cooled to room temperature, added ether, washed with water and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300; hexane:ethyl acetate=100:1-100:2) to provide the title compound (1.32 g, 43%).

Source