(1,1'-Biphenyl)-2-ol → HCID 66845232, Verbindung

HRID 1916420Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1916420
[C:1]1(C2C=CC=CC=2O)C=CC=C[CH:2]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:20]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:21][C:22]([O-:24])=[O:23].[Cl:29][C:30]1[CH:35]=[C:34]([F:36])[C:33](I)=[CH:32][C:31]=1[F:38].O1CCCC1>[NH4+].[Cl-].CCOC(C)=O.[Cu]I>[Cl:29][C:30]1[C:31]([F:38])=[CH:32][C:33]([CH:21]([C:22]([O:24][CH2:1][CH3:2])=[O:23])[C:20]([O:26][CH2:27][CH3:28])=[O:25])=[C:34]([F:36])[CH:35]=1

Komponenten

9

Edukt 5

HCID 7017(1,1'-Biphenyl)-2-olHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 3595298Propanedioic acid, monoethyl esterHCID 510000881-Chloro-2,5-difluoro-4-iodobenzene

Produkt 1

HCID 66845232HCID 66845232, VerbindungAusbeute 388,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Copper(I) iodide (69.4 mg, 0.364 mmol), 2-phenylphenol (93.0 mg, 0.546 mmol) and cesium carbonate (1.78 g, 5.46 mmol) were added to a dry flask under nitrogen. Ethyl malonate (1.11 mL, 7.29 mmol) was added to the mixture, followed by 1-chloro-2,5-difluoro-4-iodobenzene (1.00 g, 3.64 mmol) in tetrahydrofuran (3.64 mL, 44.9 mmol). The reaction mixture was sealed and heated to 90° C. After 12 hours, the reaction mixture was allowed to cool to room temperature and then diluted with saturated NH4Cl and EtOAc. The organic layer was separated, dried and filtered through Celite. The brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane) to give diethyl 2-(4-chloro-2,5-difluorophenyl)malonate (0.65 g, 58%). 1H NMR (400 MHz, CDCl3) δ 7.37 (dd, J=6.3, 9.3, 1H), 7.17 (dd, J=6.1, 8.9, 1H), 4.91 (s, 1H), 4.33-4.14 (m, 4H), 1.28 (t, J=7.2, 6H).

Aufarbeitung

  1. customThe reaction mixture was sealed
  2. temperatureto cool to room temperature
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered through Celite
  6. customThe brown oil was purified via silica gel chromatography (0-30% EtOAc-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-03a09f6221314ae6a2225c77d8c7daca
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618097B2

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