Ethyl Acetate → HCID 67359723, compound

HRID 238954Notes

Reaction equation

HRID 238954 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:19][C:16]2[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 97324-FluorophenolHCID 11430Potassium CarbonateHCID 696914-Chloro-2-fluoro-1-nitrobenzene

Product 1

HCID 67359723HCID 67359723, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 4-chloro-2-fluoronitrobenzene (3.0 g, 17.0 mmol) in DMF (8.7 mL), 4-fluorophenol (2.0 g, 17.9 mmol) and potassium carbonate (2.46 g, 17.9 mmol) were successively added, and the mixture was stirred at 70° C. for 2 hours. After the reaction, the mixture was cooled to room temperature and ethyl acetate was added to the mixture. 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 4-chloro-2-(4-fluorophenoxy)-1-nitrobenzene as a crude product. The obtained compound was used for the subsequent reaction without further purification.

Workup

  1. customAfter the reaction
  2. temperaturethe 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-29e8740d03c3456f902ba2766877a85f
Source dataset
uspto-grants-2014_02
Patent number
US08642640B2

Reaction notes

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