Chlorosuccinimide → 2-Fluoro-N-hydroxybenzimidoyl chloride

HRID 1521050Notes

Reaction equation

HRID 1521050 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1/[CH:4]=[N:5]\[OH:6].[Cl:11]N1C(=O)CCC1=O>CN(C=O)C>[OH:6]/[N:5]=[C:4](\[Cl:11])/[C:3]1[CH:7]=[CH:8][CH:9]=[CH:10][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 5372467(NZ)-N-[(2-fluorophenyl)methylidene]hydroxylamine

Product 1

HCID 96345772-Fluoro-N-hydroxybenzimidoyl chlorideYield 250.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (E)- and/or (Z)-2-fluoro-benzaldehyde oxime (66.8 g, 480 mmol) in DMF (334 mL) was added N-chlorosuccinimide (29.4 g, 211 mmol) portionwise and after 10 min, keeping the temperature below 50° C., N-chlorosuccinimide (44.1 g, 317 mmol) was added portionwise. The reaction mixture was stirred at room temperature for 2 h and then extracted with tert-butyl methyl ether to afford the title compound (91.9 g, 91%) which was obtained as a yellow oil. 1H-NMR (CDCl3): 7.10-7.25 (m, 2H), 7.40-7.50 (m, 1H), 7.64-7.70 (m, 3H), 8.99 (s, 1H).

Workup

  1. additionwas added portionwise
  2. extractionextracted with tert-butyl methyl ether

Sources & evidence

ORD record
ord-4b965ef1b7bf4310b59a7fd131f46afc
Source dataset
uspto-grants-2015_07
Patent number
US09073908B2

Reaction notes

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