Sodium Carbonate → Methyl 6-fluoro-2'-hydroxy[1,1'-biphenyl]-3-carboxylate

HRID 2101202Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2101202
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6](Br)[CH:5]=1.CC1(C)C(C)(C)OB([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])O1.C(=O)([O-])[O-].[Na+].[Na+].N1C=CN=N1>C(OCC)(=O)C.O.C(O)CC.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[OH:27])[CH:5]=1

Komponenten

9

Edukt 4

HCID 10340Sodium CarbonateHCID 27346222-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenolHCID 7018022Methyl 3-bromo-4-fluorobenzoateHCID 178418936HCID 178418936, Verbindung

Produkt 1

HCID 53218663Methyl 6-fluoro-2'-hydroxy[1,1'-biphenyl]-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 10311-PropanolLösungsmittelHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2 g (8.45 mmol) of methyl-3-bromo-4-fluorobenzoate in 28 Ml of toluene at RT was added 0.49 g (0.42 mmol) of tetrakis(triphenyl phosphine)palladium(0), 1.95 g (8.9 mmol) of 2-(4,4,5,5,-tetramethyl-1.3.2-dioxaborolan-2-yl)phenol, 5.1 Ml (10.15 mmol) of 2M aqueous sodium carbonate solution and 14 Ml of n-propanol. The reaction mixture was heated at reflux for 18 h. The reaction mixture was cooled and diluted with ethyl acetate and water. The organic fraction was separated and washed with saturated NaCl solution (brine), dried over MgSO4, filtered and the filtrate was concentrated to an oil which was purified by chromatography (silica, 90:1, 30:1 successively CH2Cl2:acetone) to give the title compound. Mass Spectrum (ESI) m/e (M+1): 247.0.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. temperatureThe reaction mixture was cooled
  4. customThe organic fraction was separated
  5. washwashed with saturated NaCl solution (brine)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated to an oil which
  9. customwas purified by chromatography (silica, 90:1, 30:1 successively CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-b49060235a6b4ad3b98e0c16f3789891
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07572822B2

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