Potassium Carbonate → 4-(4-Nitro-3-hydroxy-2,5,6-trifluoro-phenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluoro-biphenyl

HRID 1870623Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1870623
[CH2:1]([O:8][C:9]([C:11]1[CH:38]=[CH:37][C:14]([O:15][C:16]2[C:21]([F:22])=[C:20]([F:23])[C:19]([C:24]3[C:29]([F:30])=[C:28]([F:31])[C:27](F)=[C:26]([F:33])[C:25]=3[F:34])=[C:18]([F:35])[C:17]=2[F:36])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:39]([C:42]1[C:47](F)=[C:46]([F:49])[C:45]([OH:50])=[C:44]([F:51])[C:43]=1[F:52])([O-:41])=[O:40].C(=O)([O-])[O-:54].[K+].[K+].C(=O)([O-])O.[K+]>CS(C)=O>[N+:39]([C:42]1[C:43]([F:52])=[C:44]([F:51])[C:45]([O:50][C:27]2[C:28]([F:31])=[C:29]([F:30])[C:24]([C:19]3[C:20]([F:23])=[C:21]([F:22])[C:16]([O:15][C:14]4[CH:37]=[CH:38][C:11]([C:9]([O:8][CH2:1][C:2]5[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=5)=[O:10])=[CH:12][CH:13]=4)=[C:17]([F:36])[C:18]=3[F:35])=[C:25]([F:34])[C:26]=2[F:33])=[C:46]([F:49])[C:47]=1[OH:54])([O-:41])=[O:40]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 516893Potassium BicarbonateHCID 6110932,3,5,6-Tetrafluoro-4-nitrophenolHCID 108752444-(4-Benzyloxycarbonylphenoxy)nonafluorobiphenyl

Produkt 1

HCID 232955484-(4-Nitro-3-hydroxy-2,5,6-trifluoro-phenoxy)-4'-(4-benzyloxycarbonylphenoxy)octafluoro-biphenylAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

50 g of 4-(4-benzyloxycarbonylphenoxy)nonafluoro-biphenyl prepared as described in Example 3 (0.092 mol) and 19.4 g of 4-nitrotetrafluorophenol prepared as described in Example 4 (0.092 mol) are dissolved in 400 ml of dimethyl sulfoxide. 25 g of potassium carbonate (0.184 mol) are added in portions to the solution. The mixture is then stirred at room temperature for 24 hours and then heated at 60° C. for 24 hours, and 10 g of potassium hydrogencarbonate (0.1 mol) are then added. The reaction solution is ten cooled to room temperature and filtered through a fluted filter. The crude product is washed by shaking with 300 ml of ethyl acetate and 700 ml of water, and the organic phase is washed three times with water and evaporated in a rotary evaporator until the reaction product precipitates out. The reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1) and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet (yield: 92%).

Aufarbeitung

  1. customprepared
  2. temperatureheated at 60° C. for 24 hours
  3. temperaturecooled to room temperature
  4. filtrationfiltered through
  5. filtrationa fluted filter
  6. washThe crude product is washed
  7. stirringby shaking with 300 ml of ethyl acetate and 700 ml of water
  8. washthe organic phase is washed three times with water
  9. customevaporated in a rotary evaporator until the reaction product
  10. customprecipitates out
  11. customThe reaction product is then recrystallized from a mixture of ethyl acetate and n-hexane (volume ratio 1:1)
  12. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  13. customdrying cabinet (yield: 92%)

Quellen und Nachweise

ORD-Eintrag
ord-ca6e8e0c5a99436caf1c2d4e076d59ec
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06096921

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