Water → 3,4-Dichloro-5-fluoro-2-picoline
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
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- extractionthe resultant aqueous mixture is extracted with methylene chloride
- dry with materialThe organic solution is dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- distillationdistilled
Sources & evidence
- ORD record
- ord-20d8845c065944d7b6c7876a6f4dfe9b
- Source dataset
- uspto-grants-1996_12
- Patent number
- US05580872
Reaction notes
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