Dimethylformamide → 3-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrile

HRID 1614415Notes

Reaction equation

HRID 1614415 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[C:7]([F:19])=[C:8]([CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[C:9]([NH2:11])=O.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>CCCCC>[Cl:5][C:6]1[C:7]([F:19])=[C:8]([CH:12]=[C:13]([C:15]([F:17])([F:18])[F:16])[CH:14]=1)[C:9]#[N:11]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 27737463-chloro-2-fluoro-5-(trifluoromethyl)benzamide

Product 1

HCID 197738243-Chloro-2-fluoro-5-(trifluoromethyl)benzonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Procedure

Thionyl chloride, 6.0 g (50 mmol) was added to a slurry of 4.0 g (16 mmol) 3-chloro-2-fluoro-5-(trifluoromethyl) benzamide and 15 mL dimethylformamide at 0° C. After stirring for one 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 3-chloro-2-fluoro-5-(trifluoromethyl) benzonitrile in 71% yield, bp 75°-85° C./20 mm Hg.

Workup

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

Sources & evidence

ORD record
ord-ba2efb7eac4e419c9e325dd9a71aea9a
Source dataset
uspto-grants-1993_03
Patent number
US05196593

Reaction notes

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