Acetic Anhydride → 4'-Cyano-2',3'-difluoroacetanilide

HRID 1607190Notes

Reaction equation

HRID 1607190 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=1[F:11].[CH3:12][C:13](OC(C)=O)=[O:14]>>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][C:13](=[O:14])[CH3:12])=[C:3]([F:11])[C:4]=1[F:10])#[N:7]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 146210384-Amino-2,3-difluorobenzonitrile

Product 1

HCID 146210394'-Cyano-2',3'-difluoroacetanilideYield 67%

Procedure

A mixture of 9.59 g of 4-amino-2,3-difluorobenzonitrile and 20 mL of Ac2O is heated for 1 hour on a steam bath. The red solution is cooled in an ice bath and the resulting faint pink crystals filtered off, washed with 2×10 mL of Et2O and air dried. In this manner there is obtained 8.26 g (67% yield) of 4'-cyano-2',3'-difluoroacetanilide, m.p. 175°-177° C. with the appropriate NMR and IR spectral data and an ion at 197 in the mass spectrum.

Workup

  1. temperatureis heated for 1 hour on a steam bath
  2. temperatureThe red solution is cooled in an ice bath
  3. filtrationthe resulting faint pink crystals filtered off
  4. washwashed with 2×10 mL of Et2O and air
  5. customdried

Sources & evidence

ORD record
ord-9046039ea6134c44b65b313fcee31413
Source dataset
uspto-grants-1989_09
Patent number
US04863959

Reaction notes

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