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

HRID 434048Notes

Reaction equation

HRID 434048 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].[Cl:12]N1C(=O)CCC1=O>CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:3]=1[C:4](=[N:5][OH:6])[Cl:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 27733254-Bromo-2-fluorobenzaldehyde oxime

Product 1

HCID 734619254-Bromo-2-fluoro-N-hydroxybenzenecarboximidoyl chlorideYield 81.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a fashion similar to that for preparation 14, 2-Fluoro-4-bromo-benzaldehyde oxime (2.77 g, 12.7 mmol), N-chlorosuccinimide (1.76 g, 13.2 mmol), and DMF (25 ml) gave 2-fluoro-4-bromo-benzoyl chloride oxime (2.61 g, 81%) after filtration through a plug of silica gel eluting with hexanes/Et2O.

Sources & evidence

ORD record
ord-75de2550fe8440dca69b4457c541a5f2
Source dataset
uspto-grants-2003_12
Patent number
US06670373B1

Reaction notes

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