Water → HCID 22031761, compound

HRID 1792444Notes

Reaction equation

HRID 1792444 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=O)=[CH:4][CH:3]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18]C#N)=[CH:14][CH:13]=1.[OH-].[Na+].O>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2=[N:8][O:10][C:18]([C:15]3[CH:16]=[CH:17][C:12]([F:11])=[CH:13][CH:14]=3)=[C:6]2[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 114661-Bromo-4-nitrobenzeneHCID 14798Sodium HydroxideHCID 68016Benzeneacetonitrile, 4-fluoro-

Product 1

HCID 22031761HCID 22031761, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13 g 1-bromo-4-nitrobenzene, 7.68 mL 2-(4-fluorophenyl)acetonitrile and 3.9 g sodium hydroxide were stirred in 130 mL ethanol at 40° C. for 24 hours. After the reaction solution was left and cooled, water was added thereto and the reaction solution was extracted with ethylacetate. The organic solvent was washed with brine and dried over sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) and then recrystallized from hexane/ethyl acetate to give 2.9 g of the title compound as pale brown crystals.

Workup

  1. waitAfter the reaction solution was left
  2. temperaturecooled
  3. extractionthe reaction solution was extracted with ethylacetate
  4. washThe organic solvent was washed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)
  8. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-e03a8a5d6a4d424ba1fe1ef24c7a44ef
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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