HCID 22451127, compound → HCID 22451125, compound

HRID 2185625Notes

Reaction equation

HRID 2185625 reaction equation
[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([N+:18]([O-])=O)=[CH:13][C:3]=1[O:4][C:5]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]1>[Fe].C(O)(=O)C.O>[Cl:1][C:2]1[CH:16]=[C:15]([F:17])[C:14]([NH2:18])=[CH:13][C:3]=1[O:4][C:5]1([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 22451127HCID 22451127, compound

Product 1

HCID 22451125HCID 22451125, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

The obtained ethyl 1-(2-chloro-4-fluoro-5-nitro-phenoxy)cyclopropanecarboxylate (1 equivalent) is added dropwise to a mixture of acetic acid/ water (1/1) containing iron powders (3 equivalents) at 6° C. After completion of addition, the mixture is allowed to cool to room temperature and extracted with ethyl acetate. After concentrating the organic layer, the residue is subjected to chromatography to give ethyl 1-(2-chloro-4-fluoro-5-aminophenoxy)cyclopropanecarboxylate.

Workup

  1. additionAfter completion of addition
  2. extractionextracted with ethyl acetate
  3. concentrationAfter concentrating the organic layer

Sources & evidence

ORD record
ord-ce1c7e13cdbf4e48ad940290f9573f87
Source dataset
uspto-grants-2002_06
Patent number
US06403534B1

Reaction notes

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