2,6-Difluorobenzonitrile → 2-Fluoro-6-(2,6-difluorophenylamino)benzonitrile

HRID 1826840Notes

Reaction equation

HRID 1826840 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[C:3]=1[NH2:4].[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14]>CS(C)=O>[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:4][C:3]2[C:2]([F:1])=[CH:8][CH:7]=[CH:6][C:5]=2[F:9])[C:12]=1[C:13]#[N:14]

Participants

4

Reactant 2

HCID 746952,6-DifluorobenzonitrileHCID 796472,6-Difluoroaniline

Product 1

HCID 221362272-Fluoro-6-(2,6-difluorophenylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

2,6-Difluoroaniline (1.29 g, 10 mmol) was dissolved in dimethyl sulfoxide (10 mL) and stirred under argon at room temperature. Sodium hydride, dry, 95%, (0.24 g, 10 mmol) was added in portions and the mixture was stirred at room temperature for 1 hour. 2,6-Difluorobenzonitrile (0.463 g, 3.3 mmol) dissolved in dimethyl sulfoxide (5 mL) was added and the mixture stirred at room temperature for 1.5 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic phase was washed with water (5×), brine (1×), dried over anhydrous Na2SO4, filtered, and evaporated to give the crude product which was then chromatographed on silica gel eluted with 0–25% CH2Cl2 in hexane to give the title compound as a white amorphous solid. mp 145–146° C.

Workup

  1. dry with materialSodium hydride, dry
  2. addition95%, (0.24 g, 10 mmol) was added in portions
  3. stirringthe mixture was stirred at room temperature for 1 hour
  4. additionwas added
  5. stirringthe mixture stirred at room temperature for 1.5 hours
  6. customThe reaction mixture was partitioned between ethyl acetate and water
  7. washthe organic phase was washed with water (5×), brine (1×)
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. customevaporated
  11. customto give the crude product which
  12. customwas then chromatographed on silica gel
  13. washeluted with 0–25% CH2Cl2 in hexane

Sources & evidence

ORD record
ord-b7a6d7a3acb64287b4d46c4246080b82
Source dataset
uspto-grants-2006_05
Patent number
US07053099B1

Reaction notes

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