Chlorosuccinimide → 4-Fluoro-N-hydroxybenzimidoyl chloride

HRID 332024

Reaction equation

HRID 332024 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 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)- and/or (Z)-4-fluoro-benzaldehyde oxime (100 g, 719 mmol) in DMF (500 mL) was added N-chlorosuccinimide (110 g, 791 mmol) portionwise keeping the temperature below 70° C. The reaction mixture was stirred at room temperature for 2.5 h and then extracted with tert-butyl methyl ether to afford the title compound (125 g, 100%) which was obtained as a yellow oil. MS: m/e=173.1 [M]+.

Workup

  1. customthe temperature below 70° C
  2. extractionextracted with tert-butyl methyl ether

Sources & evidence

ORD record
ord-53437734b7194a19952a60218c251162
Source dataset
uspto-grants-2014_11
Patent number
US08877782B2

Linked notes

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