Ethyl Acetate → HCID 58483015, compound

HRID 238955Notes

Reaction equation

HRID 238955 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:3]=1.[Cl-].[NH4+].C(OCC)(=O)C>C(O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 67359723HCID 67359723, compound

Product 1

HCID 58483015HCID 58483015, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-2-(4-fluorophenoxy)-1-nitrobenzene (4.56 g, 17.0 mmol) and iron powder (3.07 g, 55.0 mmol) in ethanol (20 mL), a saturated aqueous ammonium chloride solution (aq., 8.0 mL) was added, and the mixture was stirred at 90° C. for 30 minutes. After the reaction, the reaction mixture was cooled to room temperature, and ethyl acetate (30 mL) was added. After the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it was dried with sodium sulfate. The solvent was distilled off under reduced pressure to give the title compound (3.62 g, 90%). The obtained compound was used for the subsequent reaction without further purification.

Workup

  1. customAfter the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. washAfter the organic phase was washed with water (30 mL), 1N sodium hydroxide (aq., 30 mL) and saturated brine (20 mL), it
  4. dry with materialwas dried with sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5636dc668b7c4a8d90771a07b56ef814
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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