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Acetonitrile → 4-(Biphenyl-2-yloxy)-3,5,6-trichlorophthalonitrile

HRID 525841
Notes
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Reaction equation

HRID 525841 reaction equation
[Cl:1][C:2]1[C:3](Cl)=[C:4]([Cl:13])[C:5]([Cl:12])=[C:6]([C:10]#[N:11])[C:7]=1[C:8]#[N:9].[C:15]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]([OH:21])=[CH:17][CH:18]=[CH:19][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(OCC)(=O)C>[C:15]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][C:3]1[C:2]([Cl:1])=[C:7]([C:8]#[N:9])[C:6](=[C:5]([Cl:12])[C:4]=1[Cl:13])[C:10]#[N:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7017(1,1'-Biphenyl)-2-olHCID 11430Potassium CarbonateHCID 160571,2-Benzenedicarbonitrile, 3,4,5,6-tetrachloro-

Product 1

HCID 1179027074-(Biphenyl-2-yloxy)-3,5,6-trichlorophthalonitrile

Reagents, catalysts & solvents 1

HCID 8857
Ethyl Acetate
Solvent

Procedure

To a 250 mL flask, 4.8 g of tetrachlorophthalonitrile, 4.3 g of biphenyl-2-ol, 5 g of potassium carbonate (K2CO3) and 55 mL of acetonitrile are added, followed by heating for 12 hours while refluxing. After completion of the reaction, 30 mL of ethyl acetate is added and filtered to remove the solvent. To the obtained solid, a suitable amount of dichloromethane is added to dissolve the solid, followed by adding hexane for crystallization. The obtained solid is filtered and dried under vacuum to obtain a compound, 4-[(biphenyl-2-yl)oxy]-3,5,6-trichlorophthalonitrile. The second step reaction may be represented by Reaction Scheme 2:

Workup

  1. temperatureby heating for 12 hours
  2. temperaturewhile refluxing
  3. additionis added
  4. filtrationfiltered
  5. customto remove the solvent
  6. additionTo the obtained solid, a suitable amount of dichloromethane is added
  7. dissolutionto dissolve the solid
  8. additionby adding hexane
  9. customfor crystallization
  10. filtrationThe obtained solid is filtered
  11. customdried under vacuum

Sources & evidence

ORD record
ord-9f221331d5624b8793ac8825c68b4545
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09341743B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes