Tetrachloro-p-hydroquinone → 1,4-Bis(3,4-dicyanotrifluorophenoxy)tetrachlorobenzene

Temperature

80 °C

In a 500 ml 4-necked flask, were poured 71.15 g (355 mmol) of tetrafluorophthalonitrile, 2.16 g (37.1 mmol) of potassium fluoride and 210 g of acetonitrile, and resulting was heated to 80° C. This mixture was kept at 80° C. with stirring, and to this mixture were dropped 4.40 g (17.7 mmol) of tetrachlorohydroquinone in 200 ml of acetonitrile over 1 hour. After dropping, reaction was performed at 80° C. for 6 hours. The reaction solution was cooled, filtrated, and the resulting residue washed with 30 ml and 15 ml of acetonitrile. After the filtrate had been concentrated on an evaporator to remove the solvent, 62.34 g of tetrafluorophthalonitrile was removed under in vacuo. To this was poured 27 ml of toluene and reflux performed for 1 hour. After cooling, the residue was washed with 5 ml, 25 ml and 5 ml of toluene, respectively, and further 12 ml of deionized water for three times. Finally, by drying the residue at 70° C. in vacuo, 9.08 g of 1,4-bis(3,4-dicyanotrifluorophenoxy)tetrachlorobenzene were obtained (yield: 84%).

1. customresulting
2. customwas kept at 80° C.
3. customreaction
4. temperatureThe reaction solution was cooled
5. filtrationfiltrated
6. washthe resulting residue washed with 30 ml and 15 ml of acetonitrile
7. concentrationAfter the filtrate had been concentrated on an evaporator
8. customto remove the solvent, 62.34 g of tetrafluorophthalonitrile
9. customwas removed under in vacuo
10. additionTo this was poured 27 ml of toluene
11. temperaturereflux
12. waitperformed for 1 hour
13. temperatureAfter cooling
14. washthe residue was washed with 5 ml, 25 ml and 5 ml of toluene
15. customFinally, by drying the residue at 70° C. in vacuo

ORD record

ord-c4b94c6ced3e49f886b5d1c0500496f8

Source dataset

uspto-grants-2007_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07217827B2