Water → 6-Chloro-3'-fluorobiphenyl-3-ol
Reaktionsgleichung
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][C:9]=1I.[F:16][C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1.O>O1CCOCC1>[Cl:7][C:8]1[C:9]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([F:16])[CH:22]=2)=[CH:10][C:11]([OH:14])=[CH:12][CH:13]=1Komponenten
6
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
Caesium carbonate (1.15 g, 3.53 mmol) was added to a solution of 4-chloro-3-iodophenol (300 mg, 2.14 mmol) and 3-fluorophenylboronic acid (330 mg, 1.30 mmol) in dioxane:water (22.5 mL:4.5 mL). The reaction mixture was degassed and tetrakistriphenylphosphine palladium (0) (69 mg, 0.06 mmol) was added. The reaction mixture was stirred at 70° C. for 5 hours. The cooled reaction mixture was concentrated in vacuo and the aqueous residue was extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo. The residue was purified on the biotage eluting with heptane:ethyl acetate (from 98:2 to 80:20) to give the title compound (270 mg, 100%) as a yellow solid.
Aufarbeitung
- customThe reaction mixture was degassed
- customThe cooled reaction mixture
- concentrationwas concentrated in vacuo
- extractionthe aqueous residue was extracted with ethyl acetate (3×10 mL)
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified on the biotage
- washeluting with heptane
Quellen und Nachweise
- ORD-Eintrag
- ord-86e26e158b3c4c0ab239898d9097551e
- Quelldatensatz
- uspto-grants-2014_07
- Patentnummer
- US08772293B2
Notizen zur Reaktion
Wird geladen…