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

HRID 1859

Reaction equation

HRID 1859 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([CH3:9])[CH:3]=1.C(O[Cl:15])(C)(C)C.O>C(Cl)(Cl)Cl>[Cl:15][C:3]1[C:4]([CH3:9])=[N:5][CH:6]=[C:7]([F:8])[C:2]=1[Cl:1]

Participants

5

Conditions

Temperature
0 °C

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.

Workup

  1. extractionthe resultant aqueous mixture is extracted with methylene chloride
  2. dry with materialThe organic solution is dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. distillationdistilled

Sources & evidence

ORD record
ord-1ecb12c0a720485081b2a903dedaad68
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Linked notes

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