Cesium carbonate → Methyl 4'-fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylate

HRID 494194

Reaktionsgleichung

Reaktionsgleichung von HRID 494194
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:9]=2[OH:18])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:25][O:26][CH2:27][CH2:28]Br>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH3:17])=[O:15])=[CH:10][C:9]=2[O:18][CH2:28][CH2:27][O:26][CH3:25])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 69037981[1,1'-Biphenyl]-4-carboxylic acid, 4'-fluoro-2-hydroxy-, methyl ester

Produkt 1

HCID 69039439Methyl 4'-fluoro-2-(2-methoxyethoxy)-1,1'-biphenyl-4-carboxylateAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of methyl 4′-fluoro-2-hydroxy-1,1′-biphenyl-4-carboxylate (D75) (400 mg, 1.6 mmol) in DMF (10 ml) was added cesium carbonate (1.27 g, 3.9 mmol) and 2-methoxyethylbromide (400 mg, 1.6 mmol) and the reaction was heated at 80° C. overnight. The solvent was evaporated and the residue was dissolved in EtOAc, washed with water and brine, then dried over MgSO4 to give the title compound (494 mg) which was used without further purification in the next step. MS(ES): (M-MeOH)H+ 273.

Aufarbeitung

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4

Quellen und Nachweise

ORD-Eintrag
ord-833d51aee49b4b84b114c243563ce9ec
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538121B2

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