Tetrafluorophthalonitrile → 1,4-Bis(3,4-dicyanotrifluorophenoxy)tetrafluorobenzene

HRID 1458283Notes

Reaction equation

HRID 1458283 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:15][C:16]1[C:21]([OH:22])=[C:20]([F:23])[C:19]([F:24])=[C:18]([OH:25])[C:17]=1[F:26].[Na].[Na]>CN(C=O)C>[C:8]([C:7]1[C:2]([F:1])=[C:3]([C:4]([F:13])=[C:5]([F:12])[C:6]=1[C:10]#[N:11])[O:22][C:21]1[C:16]([F:15])=[C:17]([F:26])[C:18]([O:25][C:3]2[C:4]([F:13])=[C:5]([F:12])[C:6]([C:10]#[N:11])=[C:7]([C:8]#[N:9])[C:2]=2[F:1])=[C:19]([F:24])[C:20]=1[F:23])#[N:9]

Participants

4

Reactant 2

HCID 74600TetrafluorophthalonitrileHCID 88247385Disodium tetrafluorohydroquinone

Product 1

HCID 111459791,4-Bis(3,4-dicyanotrifluorophenoxy)tetrafluorobenzeneYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In an Erlenmeyer flask were charged 40.0 g (0.2 mol) of tetrafluorophthalonitrile and 0.1 liter of DMF. The flask containing the mixture was immersed in an ice-water bath to keep the mixture at 0° to 5° C. To the mixture was added portionwise in 10 minutes 11.3 g (0.05 mol) of disodium tetrafluorohydroquinone. The resulting mixture was stirred at that temperature for 20 minutes and then at room temperature for 30 minutes. Thereafter, the reaction mixture was treated in the same manner as in Example 16 and the product was identified in the same manner as in Example 16. Thus 14.6 g of 1,4-bis(3,4-dicyanotrifluorophenoxy)tetrafluorobenzene was obtained in a yield of 54%.

Workup

  1. additionThe flask containing the mixture
  2. customwas immersed in an ice-water bath
  3. customat 0° to 5° C
  4. waitat room temperature for 30 minutes
  5. additionThereafter, the reaction mixture was treated in the same manner as in Example 16

Sources & evidence

ORD record
ord-2eeda7aa38b44239a12e8ffd6209aa71
Source dataset
uspto-grants-1998_12
Patent number
US05849934

Reaction notes

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