2,5-Dichlorophenol → HCID 18784286, compound

HRID 1452713Notes

Reaction equation

HRID 1452713 reaction equation
[F:1][C:2]1[C:3](F)=[C:4](F)[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][C:21]([Cl:24])=[CH:20][C:19]=1[OH:25]>CC(C)=O>[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[O:25][C:4]1[C:5]([F:12])=[C:6]([C:10]#[N:11])[C:7](=[C:2]([F:1])[C:3]=1[O:25][C:19]1[CH:20]=[C:21]([Cl:24])[CH:22]=[CH:23][C:18]=1[Cl:17])[C:8]#[N:9]

Participants

5

Reactant 3

HCID 662,5-DichlorophenolHCID 74600Tetrafluorophthalonitrile2×HCID 522689Potassium Fluoride

Product 1

HCID 18784286HCID 18784286, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent3×

Conditions

Temperature
20 °C

Procedure

Into a separable flask of glass provided with a stirrer, a thermometer, a water separation tube, and a cooling tube and having an inner volume of 300 ml, 242.5 gr of acetone and 19.1 gr (0.0955 mol) of tetrafluorophthalonitrile were placed, to dissolve tetrafluorophthalonitrile in acetone homogeneously. Next, the resultant solution and 134 gr (0.2306 mol) of potassium fluoride were added together and the resultant reaction slurry was retained at −5° C. To this reaction slurry, 34.1 gr (0.2092 mol) of 2,5-dichlorophenol dissolved uniformly in 30.5 gr of acetone was added dropwise over a period of one hour. The reaction proceeding during the dropwise addition was continued with the reaction product cooled from the exterior so as to keep the interior temperature thereof in the range of −5° C. to 0° C. After the dropwise addition was completed, the reaction mixture was retained for additional two hours. After the reaction was completed, the contents of the flask were cooled to 20° C. and filtered to separate the solid component.

Workup

  1. customInto a separable flask of glass provided with a stirrer
  2. customa thermometer, a water separation tube, and a cooling tube
  3. customthe resultant reaction slurry
  4. customwas retained at −5° C
  5. additionwas added dropwise over a period of one hour
  6. additionThe reaction proceeding during the dropwise addition
  7. temperaturecooled from the exterior so as
  8. customin the range of −5° C. to 0° C
  9. additionAfter the dropwise addition
  10. filtrationfiltered
  11. customto separate the solid component

Sources & evidence

ORD record
ord-92e36b44a09d46a890d447b9e6a74234
Source dataset
uspto-grants-2009_01
Patent number
US07473777B2

Reaction notes

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