N-methyl-2-pyrrolidone → 4-Amino-3,5-difluorobenzonitrile

HRID 1707521Notes

Reaction equation

HRID 1707521 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[C:11]([Cu])#[N:12].CN1C(=O)CCC1>O>[NH2:6][C:5]1[C:7]([F:9])=[CH:8][C:2]([C:11]#[N:12])=[CH:3][C:4]=1[F:10]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 6101914-Bromo-2,6-difluoroanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 2804674-Amino-3,5-difluorobenzonitrileYield 42.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

340 g (1.63 mol) of 4-bromo-2,6-difluoroaniline, 223 g (2.5 mol) of CuCN and 800 cm3 of NMP were refluxed for 1.5 hours on a mantle heater. The reaction solution was cooled to room temperature, and after adding 300 cm3 of EDA, it was poured into 2,000 cm3 of water, extracted with hexane, and washed with an aqueous EDA solution and ice. The hexane was removed, and the residue was distilled under reduced pressure (b. p. 143° C./6mmHg) to obtain 108 g (0.7 mol) of 4-amino-3,5-difluorobenzonitrile.

Workup

  1. additionafter adding 300 cm3 of EDA, it
  2. extractionextracted with hexane
  3. washwashed with an aqueous EDA solution and ice
  4. customThe hexane was removed
  5. distillationthe residue was distilled under reduced pressure (b. p. 143° C./6mmHg)

Sources & evidence

ORD record
ord-22a29cfb5e10414086abf79246b1cbfa
Source dataset
uspto-grants-1994_10
Patent number
US05354502

Reaction notes

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