Reaction #1955

Reaction equation

water

4-chloro-5-fluoro-2-picoline

product

4-Chloro-5-fluoro-2-picoline

t-butylhypochlorite

→

title compound

3,4-Dichloro-5-fluoro-2-picoline

Solvents

chloroform

Conditions

Workup

1. 1
   Extractionthe resultant aqueous mixture is extracted with methylene chloride
2. 2
   DryingThe organic solution is dried over anhydrous magnesium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   workup.DISTILLATIONdistilled

Procedure

To 0.87 g (6 mmol) of 4-chloro-5-fluoro-2-picoline, the product of Example 66, in 20 mL of chloroform cooled to -45° C., is added 0.75 mL of t-butylhypochlorite. The reaction mixture is stirred at -45° C. for 2 hours and at 0° C. for 2 hours. The reaction mixture is then poured into water and the resultant aqueous mixture is extracted with methylene chloride. The organic solution is dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and distilled to afford the title compound.

Source