Chlorosuccinimide → 4-Bromo-2-fluoro-N-hydroxybenzenecarboximidoyl chloride

HRID 1988895Notes

Reaction equation

HRID 1988895 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:18]=[CH:17][C:13]([CH:14]=[N:15][OH:16])=[C:12]([F:19])[CH:11]=1>CN(C=O)C>[Br:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([Cl:1])=[N:15][OH:16])=[C:12]([F:19])[CH:11]=1

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 27733254-Bromo-2-fluorobenzaldehyde oxime2×

Product 1

HCID 734619254-Bromo-2-fluoro-N-hydroxybenzenecarboximidoyl chlorideYield 324.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Chlorosuccinimide (0.075 g) was added to a solution of 4-bromo-2-fluorobenzaldehyde oxime (Intermediate 50) (0.44 g) in DMF (1 ml) then heated for several minutes at 55°. The mixture was allowed to cool to <50° then more N-chlorosuccinimide (0.22 g) was added. After a few minutes the mixture was allowed to cool to room temp. then partitioned between water and ether. The layers were separated, the aqueous layer was re-extracted with ether (×2) and the combined organic extracts were washed with water and brine, dried (MgSO4) and concentrated under vacuum to give a white solid (0.46 g).

Workup

  1. temperaturethen heated for several minutes at 55°
  2. temperatureto cool to <50°
  3. waitAfter a few minutes the mixture was allowed
  4. temperatureto cool to room temp.
  5. customthen partitioned between water and ether
  6. customThe layers were separated
  7. extractionthe aqueous layer was re-extracted with ether (×2)
  8. washthe combined organic extracts were washed with water and brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ef8c5f8133b34fbb9b7e81c75da7504d
Source dataset
uspto-grants-2010_01
Patent number
US07642276B2

Reaction notes

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