1-(2-Bromo-4-fluoro-phenyl)-butane-1,4-diol → 2-(2-Bromo-4-fluoro-phenyl)-tetrahydro-furan

HRID 558135

Reaktionsgleichung

Reaktionsgleichung von HRID 558135
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:14])[CH2:10][CH2:11][CH2:12]O>ClCCCl.C(Cl)(Cl)Cl.CC(O)C.F[Sb-](F)(F)(F)(F)F.[Ag+].[Pt](Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:10][CH2:11][CH2:12][O:14]1

Komponenten

6

Edukt 1

HCID 574450901-(2-Bromo-4-fluoro-phenyl)-butane-1,4-diol

Produkt 1

HCID 574450912-(2-Bromo-4-fluoro-phenyl)-tetrahydro-furanAusbeute 77,3 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 2770Platinous chlorideKatalysatorHCID 16687962Silver hexafluoroantimonateKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 21906603Chloroform isopropyl alcoholLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Combine 1-(2-bromo-4-fluoro-phenyl)-butane-1,4-diol (1 g, 3.8 mmol), silver (I)hexafluoroantimonate (131 mg, 0.4 mmol), platinum(II) chloride (40 mg, 0.2 mmol) in 1,2-dichloroethane (10 mL) in a pressure tube. Seal the tube and heat the mixture overnight at 110° C. Dilute the mixture with chloroform-IPA (3:1, 100 mL). Wash the organic phase with aqueous saturated sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (20% ethyl acetate in hexane) to give the title compound as a pale yellow oil (0.72 g, 77%).

Aufarbeitung

  1. customSeal the tube
  2. washWash the organic phase with aqueous saturated sodium chloride and water
  3. dry with materialDry the mixture over sodium sulfate
  4. concentrationConcentrate the solution in vacuo
  5. customPurify by column chromatography (20% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-95ac991e75c34e8f80fa54d834ab4ec3
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063035B2

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