Dimethylformamide → 2,3-Difluoro-5-(trifluoromethyl)benzonitrile

HRID 1614418Notes

Reaction equation

HRID 1614418 reaction equation
S(Cl)(Cl)=O.[F:5][C:6]1[C:14]([F:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:7]=1[C:8]([NH2:10])=O.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>CCCCC>[F:5][C:6]1[C:14]([F:15])=[CH:13][C:12]([C:16]([F:19])([F:17])[F:18])=[CH:11][C:7]=1[C:8]#[N:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 19773828HCID 19773828, compound

Product 1

HCID 190908472,3-Difluoro-5-(trifluoromethyl)benzonitrileYield 56%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Thionyl chloride, 6.0 g (50 mmol) was added to a slurry of 4.0 g (18 mmol) 2,3-difluoro-5-(trifluoromethyl)benzamide and 15 mL dimethylformamide at 0° C. After stirring for 1 hour, the reaction mixture was diluted with 25 mL pentane and neutralized by dropwise addition of a saturated potassium carbonate solution and filtered. The pentane solution was dried and distilled to yield 2,3-difluoro-5-(trifluoromethyl) benzonitrile in 56% yield, bp 65°-70° C./20 mm Hg.

Workup

  1. filtrationfiltered
  2. dry with materialThe pentane solution was dried
  3. distillationdistilled

Sources & evidence

ORD record
ord-c908633bde49442cb0736bc839a25c86
Source dataset
uspto-grants-1993_03
Patent number
US05196593

Reaction notes

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