Hydrochloric Acid → 4-Amino-3,5-difluorobenzonitrile

HRID 1086395Notes

Reaction equation

HRID 1086395 reaction equation
Br[C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1.[Cu][C:12]#[N:13].CN1CCCC1=O.Cl>[Fe](Cl)(Cl)Cl.O>[C:12]([C:2]1[CH:8]=[C:7]([F:9])[C:5]([NH2:6])=[C:4]([F:10])[CH:3]=1)#[N:13]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 6101914-Bromo-2,6-difluoroanilineHCID 178418546HCID 178418546, compound

Product 1

HCID 2804674-Amino-3,5-difluorobenzonitrileYield 57.3%

Reagents, catalysts & solvents 2

HCID 24380Iron chloride (FeCl3)CatalystHCID 962WaterSolvent

Procedure

132 g of 4-bromo-2,6-difluoroaniline, 70 g of copper (I) cyanide and 444 ml of N-methylpyrrolidone were mixed in a flask and refluxed for 3 hours. The reaction solution was poured into a solution including 266 g of iron (III) chloride, 85 ml of concentrated hydrochloric acid and 315 ml of water. The solution was extracted with chloroform and washed with water and an aqueous 10% solution of potassium hydroxide. The chloroform was distilled off. The residue was distillated under a reduced pressure (bp: 90°-110° C./4 mmHg) and recrystallized from a solvent mixture of hexane and chloroform, to yield 56 g of 4-cyano-2,6-difluoroaniline.

Workup

  1. temperaturerefluxed for 3 hours
  2. additionThe reaction solution was poured into a solution
  3. extractionThe solution was extracted with chloroform
  4. washwashed with water
  5. distillationThe chloroform was distilled off
  6. customrecrystallized from a solvent mixture of hexane and chloroform

Sources & evidence

ORD record
ord-7d057a252a304ed7a53ba0930e8f5a03
Source dataset
uspto-grants-1991_07
Patent number
US05030382

Reaction notes

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