Tetrafluorophthalonitrile → 3,5,6-Trifluoro-4-(2-(2,4-dimethyl-3-pentyloxy)carbonyl-6-phenylphenoxy)phthalonitrile

HRID 610460

Reaction equation

HRID 610460 reaction equation
[F:1][C:2]1[C:9]([F:10])=[C:8](F)[C:7]([F:12])=[C:4]([C:5]#[N:6])[C:3]=1[C:13]#[N:14].[CH3:15][CH:16]([CH:18]([O:22][C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:26]=1[OH:37])=[O:24])[CH:19]([CH3:21])[CH3:20])[CH3:17].[F-].[K+]>C(#N)C>[F:12][C:7]1[C:8]([O:37][C:26]2[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:28][CH:29]=[CH:30][C:25]=2[C:23]([O:22][CH:18]([CH:19]([CH3:21])[CH3:20])[CH:16]([CH3:15])[CH3:17])=[O:24])=[C:9]([F:10])[C:2]([F:1])=[C:3]([C:13]#[N:14])[C:4]=1[C:5]#[N:6]

Participants

5

Reactant 3

HCID 74600TetrafluorophthalonitrileHCID 522689Potassium FluorideHCID 110560652-(2,4-Dimethyl-3-pentyloxy)carbonyl-6-phenylphenol

Product 1

HCID 118270963,5,6-Trifluoro-4-(2-(2,4-dimethyl-3-pentyloxy)carbonyl-6-phenylphenoxy)phthalonitrileYield 93.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In a four-neck flask having an inner volume of 100 ml, 3.00 g (15 m.mols) of 3,4,5,6-tetrafluorophthalonitrile, 4.69 g (15 m.mols) of 2-(2,4-dimethyl-3-pentyloxy)carbonyl-6-phenylphenol, 2.62 g (45 m.mols) of potassium fluoride, and 50 ml of acetonitrile were placed and left reacting under reflux for six hours. After the reaction, the reaction mass was filtered and then distilled to expel the solvent by evaporation and obtain 6.90 g (14 m.mols) of 3,5,6-trifluoro-4-(2-(2,4-dimethyl-3-pentyloxy)carbonyl-6-phenylphenoxy)phthalonitrile as the product aimed at.

Workup

  1. customIn a four-neck flask having
  2. waitleft
  3. temperatureunder reflux for six hours
  4. customAfter the reaction
  5. filtrationthe reaction mass was filtered
  6. distillationdistilled
  7. customby evaporation

Sources & evidence

ORD record
ord-4b86f58a821b4d5791afa694cdbc2781
Source dataset
uspto-grants-1999_12
Patent number
US05998609

Linked notes

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