Ammonium Hydroxide → 5,6-Difluoro-2-benzofurancarbonitrile

HRID 618724Notes

Reaction equation

HRID 618724 reaction equation
[F:1][C:2]1[C:3]([F:14])=[CH:4][C:5]2[O:9][C:8]([C:10]([NH2:12])=O)=[CH:7][C:6]=2[CH:13]=1.P(Cl)(Cl)(Cl)=O.[OH-].[NH4+]>>[F:1][C:2]1[C:3]([F:14])=[CH:4][C:5]2[O:9][C:8]([C:10]#[N:12])=[CH:7][C:6]=2[CH:13]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 15434545HCID 15434545, compound

Product 1

HCID 218483295,6-Difluoro-2-benzofurancarbonitrileYield 88%

Procedure

1.5 g (7.61 mmol) of 5,6-difluorobenzofuran-2-carboxamide were treated with 8 ml of phosphorus oxychloride and heated under reflux over a period of 5 minutes while stirring. Subsequently, the clear solution was added dropwise while stirring to a mixture of 36 ml of ammonium hydroxide solution and 64 g of ice, with the temperature not exceeding 20°. The mixture was stirred for a further 30 minutes and the beige crystals were subsequently filtered off. There were obtained 1.2 g (88%) of 5,6-difluorobenzofuran-2-carbonitrile as a beige solid with m.p. 103°.

Workup

  1. temperatureheated
  2. temperatureunder reflux over a period of 5 minutes
  3. additionSubsequently, the clear solution was added dropwise
  4. customexceeding 20°
  5. stirringThe mixture was stirred for a further 30 minutes
  6. filtrationthe beige crystals were subsequently filtered off

Sources & evidence

ORD record
ord-3ade754ab53444cabd069ada9852a47d
Source dataset
uspto-grants-1999_09
Patent number
US05955495

Reaction notes

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