Acetonitrile → 3,6-difluoro-4,5-bisphenylthiophthalonitrile

HRID 373753Notes

Reaction equation

HRID 373753 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-:8].[K+].[C:10](#[N:12])[CH3:11]>>[F:8][C:3]1[C:2]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:1]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:6]([F:8])=[C:11]([C:10]#[N:12])[C:11]=1[C:10]#[N:12]

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 7969ThiophenolHCID 522689Potassium Fluoride

Product 1

HCID 19822433,6-difluoro-4,5-bisphenylthiophthalonitrile

Conditions

Temperature
50 °C

Procedure

In a four-neck flask having an inner volume of 200 ml, 19.6 g (98 m.mols) of 3,4,5,6 -tetrafluiorophthalonitrile, 21.6 g (196 m.mols) of thiophenol, 17.1 g (294 m.mols) of potassium fluoride (KF), and 100 ml of acetonitrile were placed and stirred at 50° C. for reaction for 12 hours. Then, the reaction mixture was cooled to room temperature. The yellow solid which formed consequently in the mixture was separated by filtration. The cake thus obtained was purified by washing first with methanol and then with hot water, to obtain 34.5 g of 3,6-difluoro-4,5-bisphenylthiophthalonitrile (yield: 92.5 mol % based on 3,4,5,6-tetrafluoronitrile).

Workup

  1. customIn a four-neck flask having
  2. temperatureThen, the reaction mixture was cooled to room temperature
  3. customThe yellow solid which formed consequently in the mixture
  4. customwas separated by filtration
  5. customThe cake thus obtained
  6. customwas purified
  7. washby washing first with methanol

Sources & evidence

ORD record
ord-fbb790d9103544168132200ae5cedd03
Source dataset
uspto-grants-1992_11
Patent number
US05166025

Reaction notes

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