4-Iodophenol → 2',4'-Difluoro(1,1'-biphenyl)-4-ol

HRID 547843Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 547843
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1B(O)O.I[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.[Pd].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1

Komponenten

7

Edukt 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 27343342,4-Difluorophenylboronic acid

Produkt 1

HCID 1009552',4'-Difluoro(1,1'-biphenyl)-4-olAusbeute 109,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 2734559Bis(tricyclohexylphosphine) palladium(0)KatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2,4-Difluoro-phenyl-boronic acid (1.29 g, 8.18 mmol) and 4-iodophenol (0.60 g, 2.7 mmol) were suspended in DMF (60 mL) and 6 mL H2O (6 mL). The mixture was degassed with nitrogen. Finely ground potassium carbonate (1.13 g, 8.18 mmol) and bis(tricyclohexylphosphine) palladium(0) (91 mg, 0.13 mmol) were added. The reaction was stirred at reflux overnight under nitrogen and cooled. The mixture was filtered through a plug of silica gel/Celite and evaporated. The residue was diluted with ethyl acetate and washed with saturated sodium bicarbonate (2×20 mL), dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography, eluting with 0-25% ethyl acetate in hexanes to yield 2′,4′-difluoro-biphenyl-4-ol (0.61 g, 100%). LR-MS (ES) calculated for C12H8F2O, 206.19; found m/z 205 [M−H]−.

Aufarbeitung

  1. customThe mixture was degassed with nitrogen
  2. temperatureat reflux overnight under nitrogen
  3. temperaturecooled
  4. filtrationThe mixture was filtered through a plug of silica gel/Celite
  5. customevaporated
  6. additionThe residue was diluted with ethyl acetate
  7. washwashed with saturated sodium bicarbonate (2×20 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by flash chromatography
  12. washeluting with 0-25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e1b4485cb6f84a0d82965dc3d4df1593
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07939569B1

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