Ammonium Chloride → HCID 69421745, compound

HRID 457539Notes

Reaction equation

HRID 457539 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]([O:15][C:16]2[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Br:24])[CH:17]=2)[C:7]=1[F:25])[CH3:2].[NH4+].[Cl-]>CCO.O.[Fe]>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[C:8]([O:15][C:16]2[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[C:18]([Br:24])[CH:17]=2)[C:7]=1[F:25])[CH3:2]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 69420270Ethyl 3-(3-bromo-5-cyanophenoxy)-2-fluoro-4-nitrobenzeneacetate

Product 1

HCID 69421745HCID 69421745, compoundYield 98.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of ester (117a, 4.34 g, 10.26 mmol), Fe powder (2.40 g, 43.07 mmol), and NH4Cl (2.30 g, 43.07 mmol) in EtOH (80 mL) and H2O (40 mL) was heated to reflux for 2 h. The solution was cooled to RT and filtered through CELITE®. The filter cake was washed with EtOAc (200 mL), the aqueous and organic layers were separated, and the organic layer was washed with brine (2×60 mL). The solution was dried with anhydrous MgSO4, and evaporated to provide 3.98 g (98%) of the [4-amino-3-(3-bromo-5-cyano-phenoxy)-2-fluoro-phenyl]-acetic acid ethyl ester (117b).

Workup

  1. temperatureto reflux for 2 h
  2. filtrationfiltered through CELITE®
  3. washThe filter cake was washed with EtOAc (200 mL)
  4. customthe aqueous and organic layers were separated
  5. washthe organic layer was washed with brine (2×60 mL)
  6. dry with materialThe solution was dried with anhydrous MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-b50fa07ed6f7421e81c1b59d1c3a4614
Source dataset
uspto-grants-2007_03
Patent number
US07189718B2

Reaction notes

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