2,4-Difluoronitrobenzene → 2-(5-Fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile

HRID 131328Notes

Reaction equation

HRID 131328 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH2:12][C:13]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:14]=1[C:15]#[N:16].O.[OH-].[Li+]>CS(C)=O>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([NH:12][C:13]2[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:17][C:14]=2[C:15]#[N:16])[CH:7]=1

Participants

5

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 168937Lithium hydroxide, monohydrateHCID 126273614-Amino-3-cyanobenzotrifluoride

Product 1

HCID 586259682-(5-Fluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrileYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
55 °C

Procedure

Combine 2,4-difluoro-1-nitro-benzene (5.36 g, 33.69 mmol), 2-amino-5-trifluoromethyl-benzonitrile (5.701 g, 30.63 mmol) and lithium hydroxide monohydrate (2.57 g, 61.25 mmol) in methyl sulfoxide (DMSO, 70 ml). Heat the resulting mixture to 55° C. for 16 hours. Cool the reaction mixture to ambient temperature, then pour into approximately 250 ml of ice water and stir for one hour. Filter the resulting mixture, wash with a large amount of water and collect the precipitate to obtain 9.53 g of the title compound (29.30 mmol, 96% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 324(M−1).

Workup

  1. temperatureCool the reaction mixture to ambient temperature
  2. filtrationFilter the resulting mixture
  3. washwash with a large amount of water
  4. customcollect the precipitate

Sources & evidence

ORD record
ord-4a758445184341b9b16bdbebbbc5707f
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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