Chlorine → 4-fluoro-N-hydroxybenzenecarboximidoyl chloride

HRID 1576983Notes

Reaction equation

HRID 1576983 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]Cl.C(=O)=O.CC(C)=O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([Cl:11])=[N:7][OH:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24526ChlorineHCID 68017N-[(4-fluorophenyl)methylidene]hydroxylamineHCID 18522661Acetone cardice

Product 1

HCID 27563164-fluoro-N-hydroxybenzenecarboximidoyl chlorideYield 48.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 25 g of 4-fluorobenzaldoxime in 200 ml of chloroform was cooled to 0° to -10°. From a pressure bottle, 14.2 g of chlorine was run into a flask cooled by dry ice-acetone and allowed to distill into the aldoxime solution, the solution being maintained at 0° ± 5°. The reaction mixture was stirred for one hour in an ice bath while nitrogen was bubbled through the solution. The chloroform was evaporated to leave an oil to which hexane was added quickly. The solid which separated was recrystallized from hexane to give 15.0 g of 4-fluorobenzohydroximoyl chloride, m.p. 74.5°-75°. The ir spectrum was consistent with the assigned structure.

Workup

  1. distillationto distill into the aldoxime solution
  2. temperaturethe solution being maintained at 0° ± 5°
  3. customwas bubbled through the solution
  4. customThe chloroform was evaporated
  5. customto leave an oil to which hexane
  6. additionwas added quickly
  7. customThe solid which separated
  8. customwas recrystallized from hexane

Sources & evidence

ORD record
ord-a0e6d7fef585480f99e86250ed1f8c19
Source dataset
uspto-grants-1976_09
Patent number
US03983246

Reaction notes

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