Water → 3,6-Difluoropyrazine-2-carbonitrile

HRID 392337Notes

Reaction equation

HRID 392337 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[C:5](S(C2C=CC=CC=2)(=O)=O)=[N:4][CH:3]=1.[F-:19].[K+].C(OCC)(=O)C.O>CS(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:19][C:5]1[C:6]([C:8]#[N:9])=[N:7][C:2]([F:1])=[CH:3][N:4]=1

Participants

7

Conditions

Temperature
60 °C

Procedure

In 4 mL of dimethyl sulfoxide was dissolved 0.40 g of 6-fluoro-3-(phenylsulfonyl)-2-pyrazinecarbonitrile. After adding 0.44 g of potassium fluoride and 0.10 g of tetra-n-butylammonium bromide successively, the mixture thus obtained was stirred at 60° C. for 1.5 hours. The reaction mixture was poured into a mixture of 20 mL of ethyl acetate and 20 mL of water, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried on anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=20:1] to obtain 0.06 g of 3,6-difluoro-2-pyrazinecarbonitrile as a colorless solid product.

Workup

  1. customthe mixture thus obtained
  2. customthe organic layer was separated
  3. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried on anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography [eluent: n-hexane:ethyl acetate=20:1]

Sources & evidence

ORD record
ord-a9313c13ab9d46d886a9c2fbeb3efc27
Source dataset
uspto-grants-2004_10
Patent number
US06800629B2

Reaction notes

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