Reaction #465981

Reaction equation

Methyl 3,6-dichloropyridine-2-carboxylate N-oxide

NaH

THF

3,5-dichlorophenol

→

white solid

Yield 76.5%

Methyl 3-Chloro-6-(3,5-dichlorophenoxy)pyridine-2-carboxylate N-oxide

Yield 76.5%

Solvents

ethyl acetate

water

Conditions

Workup

1. 1
   workup.STIRRINGstirred at RT for 3 hr
2. 2
   ExtractionThe aqueous phase was extracted with ethyl acetate (2×200 mL)
3. 3
   DryingThe combined extracts were dried (MgSO4)
4. 4
   Concentrationconcentrated

Procedure

To a dry 3-neck round bottom flask was added 60% NaH (0.432 g, 10.81 mmol), dry THF (30 mL) and 3,5-dichlorophenol (1.76 g, 10.81 mmol). The mixture was stirred until evolution of H2 (g) ceased. Methyl 3,6-dichloropyridine-2-carboxylate N-oxide (2.0 g, 9.00 mmol) was added in one portion and stirred at RT for 3 hr, diluted with ethyl acetate and 100 mL of water. The aqueous phase was extracted with ethyl acetate (2×200 mL). The combined extracts were dried (MgSO4) and concentrated to give 2.40 g of white solid.

Source