Water → HCID 26189737, compound

HRID 1505305Notes

Reaction equation

HRID 1505305 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([Cl:18])[CH:12]=2)=[CH:6][CH:5]=1)([O-])=O.[Cl-].[NH4+].O>C1COCC1.O.[Fe]>[Cl:18][C:13]1[CH:12]=[C:11]([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH:16]=[CH:15][C:14]=1[F:17]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 21528662HCID 21528662, compound2×

Product 1

HCID 26189737HCID 26189737, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 3-chloro-4-fluorophenyl 4-nitrophenyl ether (Intermediate 7, 2.48 g) in THF/water (40 mL/10 mL) was added Fe power (11.2 g, 200 mmol) and ammonium chloride (10.7 g, 200 mmol and the mixture was heated at reflux for 4 hours. After filtration, the solvent was concentrated to give a residue and poured into 50 mL of water. The mixture was extracted with ethyl acetate (3 times 50 mL) and the combined organic phases were washed and dried over magnesium sulphate. Removal of the solvent afforded the title compound (2.15 g) which was directly used in the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationAfter filtration
  4. concentrationthe solvent was concentrated
  5. customto give a residue
  6. extractionThe mixture was extracted with ethyl acetate (3 times 50 mL)
  7. washthe combined organic phases were washed
  8. dry with materialdried over magnesium sulphate
  9. customRemoval of the solvent

Sources & evidence

ORD record
ord-7f927d21e22041afb3240485b35f6935
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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