Tetrafluorophthalonitrile → HCID 23088230, compound

HRID 1452714Notes

Reaction equation

HRID 1452714 reaction equation
[F:1][C:2]1[C:3](F)=[C:4]([F:13])[C:5]([F:12])=[C:6]([C:10]#[N:11])[C:7]=1[C:8]#[N:9].[F-].[K+].[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[SH:24]>CC(=O)CC>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24][C:3]1[C:2]([F:1])=[C:7]([C:8]#[N:9])[C:6](=[C:5]([F:12])[C:4]=1[F:13])[C:10]#[N:11]

Participants

5

Reactant 3

HCID 74600Tetrafluorophthalonitrile2×HCID 80599o-ChlorothiophenolHCID 522689Potassium Fluoride

Product 1

HCID 23088230HCID 23088230, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Into a four-neck flask of glass provided with a stirrer, a thermometer, a water separation tube, and a cooling tube and having an inner volume of 100 ml, 30 gr of 2-butanone, 10 gr (0.05 mol) of tetrafluorophthalonitrile, and 3.63 gr (0.062 mol) of potassium fluoride were placed and the flask was dipped in a water bath. The reaction mixture in the reaction vessel was kept stirred at room temperature and 7.6 g (0.053 mol) of 2-chlorobenzene thiol were added thereto over about 20 minutes. The reaction temperature rose to the highest level of 30° C. When the reaction was continued for additional one hour after the completion of this addition, the conversion of tetrafluorophthalonitrile reached 99.0%. The resultant reaction solution was filtered to separate a solid component. The solid component was evaporated under a reduced pressure at 50° C. to obtain about 15 g of 2-butanone by distillation. 100 ml of methanol was added to the resultant residue of the distillation to precipitate crystals. When the crystals consequently precipitated were filtered, 11.4 gr (0.035 mol, yield: 70.2 mol %) of 4-(2-chloro phenylthio)-3,5,6-trifluorophthalonitrile was obtained.

Workup

  1. customInto a four-neck flask of glass provided with a stirrer
  2. customa thermometer, a water separation tube, and a cooling tube
  3. customthe flask was dipped in a water bath
  4. customrose to the highest level of 30° C
  5. waitWhen the reaction was continued for additional one hour
  6. additionafter the completion of this addition
  7. customThe resultant reaction solution
  8. filtrationwas filtered
  9. customto separate a solid component
  10. customThe solid component was evaporated under a reduced pressure at 50° C.
  11. customto obtain about 15 g of 2-butanone
  12. distillationby distillation
  13. addition100 ml of methanol was added to the resultant residue of the distillation
  14. customto precipitate crystals
  15. customWhen the crystals consequently precipitated
  16. filtrationwere filtered

Sources & evidence

ORD record
ord-9376cb1e906345ae933696a6ebffbcec
Source dataset
uspto-grants-2009_01
Patent number
US07473777B2

Reaction notes

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