Chlorosuccinimide → 4-Fluoro-N-hydroxybenzimidoyl chloride

HRID 872943Notes

Reaction equation

HRID 872943 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5](/[CH:6]=[N:7]\[OH:8])=[CH:4][CH:3]=1.[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[OH:8]/[N:7]=[C:6](\[Cl:11])/[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 5372466Benzaldehyde, p-fluoro-, oxime

Product 1

HCID 57063604-Fluoro-N-hydroxybenzimidoyl chlorideYield 298.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)- and/or (Z)-4-fluoro-benzaldehyde oxime (23.3 g, 167 mmol) (6.9 g, 50 mmol) in DMF (50 mL) was added N-chlorosuccinimide (6.6 g, 50 mmol) portionwise over 1 h, keeping the temperature below 35° C. The reaction mixture was stirred at room temperature for 1 h. The mixture was then poured onto ice-water, and extracted with ethyl acetate. The combined organic layers were then washed with water and brine, dried over sodium sulfate and evaporated to afford the title compound (25.9 g, 89%) which was obtained as an off white solid. MS: m/e=173.0 [M]+.

Workup

  1. customthe temperature below 35° C
  2. additionThe mixture was then poured onto ice-water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were then washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-3d8c492f7de04acd879baaced49becc2
Source dataset
uspto-grants-2015_03
Patent number
US08975397B2

Reaction notes

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