Isopropanol → 2,3',4',5'-Tetrafluorobiphenyl-4-ol

HRID 552027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552027
Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].[F:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[C:15]([F:18])[C:16]=1[F:17].C(=O)([O-])[O-].[K+].[K+].CC(O)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1.O>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([C:13]2[CH:12]=[C:11]([F:10])[C:16]([F:17])=[C:15]([F:18])[CH:14]=2)=[C:3]([F:9])[CH:4]=1

Komponenten

8

Edukt 4

HCID 3776IsopropanolHCID 11430Potassium CarbonateHCID 2734671(3,4,5-Trifluorophenyl)boronic Acid (contains varying amounts of Anhydride)HCID 27791534-Bromo-3-fluorophenol

Produkt 1

HCID 210521442,3',4',5'-Tetrafluorobiphenyl-4-olAusbeute 75,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

4-Bromo-3-fluorophenol (T-10; 5.00 g), 3,4,5-trifluorophenylboronic acid (5.07 g), potassium carbonate (10.9 g), Pd(Ph3P)2Cl2 (0.552 g), and 2-propanol were put in a reaction vessel under a nitrogen atmosphere, and heated under reflux for 5 hours. The reaction mixture was cooled to 25° C., and then poured into water (100 ml) and toluene (100 ml) and mixed. Then, the mixture was allowed to stand to be separated into two layers of organic and aqueous layers, and the extraction to an organic layer was carried out. The obtained organic layer was fractionated, washed with water, and then dried over anhydrous magnesium sulfate. The obtained solution was concentrated under reduced pressure, and the residue was purified with a fractional operation by means of column chromatography using toluene as the eluent and silica gel as the stationary phase powder. The product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11 and dried, whereby 4.79 g of 4-hydroxy-2,3′,4′,5′-tetrafluoro-1,1′-biphenyl (T-11) was obtained. The yield based on the compound (T-1) was 74%.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 5 hours
  3. additionmixed
  4. customto be separated into two layers of organic and aqueous layers
  5. extractionthe extraction to an organic layer
  6. washwashed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationThe obtained solution was concentrated under reduced pressure
  9. customthe residue was purified with a fractional operation by means of column chromatography
  10. customThe product was further purified by recrystallization from a mixed solvent of heptane/Solmix A-11
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-1e59d64b25214a84b3fd707f1ef8c6c0
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951433B2

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