Diphosgene → 4-Chloro-2-fluoro-5-{2-(ethoxycarbonylmethoxy)phenoxy}phenyl isocyanate

HRID 433730Notes

Reaction equation

HRID 433730 reaction equation
[NH2:1][C:2]1[C:3]([F:23])=[CH:4][C:5]([Cl:22])=[C:6]([CH:21]=1)[O:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].Cl[C:25](OC(Cl)(Cl)Cl)=[O:26]>C1(C)C=CC=CC=1>[Cl:22][C:5]1[C:6]([O:7][C:8]2[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=2[O:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:21][C:2]([N:1]=[C:25]=[O:26])=[C:3]([F:23])[CH:4]=1

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 86584267HCID 86584267, compound

Product 1

HCID 187593024-Chloro-2-fluoro-5-{2-(ethoxycarbonylmethoxy)phenoxy}phenyl isocyanate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Into a mixture of ethyl [2-(5-amino-2-chloro-4-fluorophenoxy)phenoxy]acetate [Intermediate compound A3-23], trichloromethyl chloroformate and toluene is added dropwise activated carbon, and the mixture is heated under reflux. The reaction solution is filtrated and the solvent is distilled off to obtain 4-chloro-2-fluoro-5-{2-(ethoxycarbonylmethoxy)phenoxy}phenyl isocyanate [Intermediate compound A12-23].

Workup

  1. additionis added dropwise activated carbon
  2. temperaturethe mixture is heated
  3. temperatureunder reflux
  4. filtrationThe reaction solution is filtrated
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-4990fe091313462e902f70c28796de67
Source dataset
uspto-grants-2003_12
Patent number
US06667413B2

Reaction notes

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