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

HRID 594925

Reaction equation

HRID 594925 reaction equation
[Cl:1][C:2]1[C:9](Cl)=[C:8]([Cl:11])[C:7]([Cl:12])=[C:4]([C:5]#[N:6])[C:3]=1[C:13]#[N:14].[C:15]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+].C(#N)C>CCCCCC.ClCCl>[C:21]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:27][C:9]1[C:2]([Cl:1])=[C:3]([C:13]#[N:14])[C:4](=[C:7]([Cl:12])[C:8]=1[Cl:11])[C:5]#[N:6]

Participants

7

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 2

HCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Procedure

3,4,5,6-tetrachlorophthalonitrile (5 g), 2-phenylphenol (3.201 g), K2CO3 (3.898 g) and acetonitrile (50 ml) are put in a 100 ml flask and then heated and refluxed. When the reaction is complete, the resultant is filtered with tetrahydrofuran (THF) to obtain a solid, the solid is added to a small amount of dichloromethane and dissolved therein, and hexane is added thereto, obtaining a crystallized solid (4-(biphenyl-2-yloxy)-3,5,6-trichlorophthalonitrile). Herein, the obtained solid is washed several times, filtered and vacuum-dried.

Workup

  1. temperatureheated
  2. temperaturerefluxed
  3. filtrationthe resultant is filtered with tetrahydrofuran (THF)
  4. customto obtain a solid
  5. dissolutiondissolved

Sources & evidence

ORD record
ord-dc90e00db95245328fecfee6e85e59a8
Source dataset
uspto-grants-2016_01
Patent number
US09242990B2

Linked notes

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