Citric Acid → 4-(2-Bromo-5-fluorophenyl)-2-hydroxy-4-methylvaleric acid-methyl ester

HRID 1374621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1374621
[CH3:1][O:2][C:3](=[O:25])[CH:4](C(=O)C1C=CC=CC=1)[CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Br:16])([CH3:8])[CH3:7].C(=O)([O-])[O-:27].[K+].[K+].S(=O)(=O)(O)O.C(=O)([O-])[O-].[Cs+].[Cs+].CI.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.CC(OC)(C)C>[CH3:1][O:2][C:3](=[O:25])[CH:4]([OH:27])[CH2:5][C:6]([C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[Br:16])([CH3:8])[CH3:7]

Komponenten

9

Edukt 6

HCID 311Citric AcidHCID 1118Sulfuric AcidHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 695164952-Benzoyl-4-(2-bromo-5-fluorophenyl)-4-methylvaleric acid-methyl ester

Produkt 1

HCID 695167344-(2-Bromo-5-fluorophenyl)-2-hydroxy-4-methylvaleric acid-methyl esterAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Versuchsvorschrift

A solution of 0.9 g (2.13 mmol) of 2-benzoyl-4-(2-bromo-5-fluorophenyl)-4-methylvaleric acid-methyl ester in 50 ml of MeOH is mixed with 1.47 g (10.6 mmol) of potassium carbonate and stirred for 3 hours at room temperature. The batch is acidified (pH 3) with 10% sulfuric acid, and it is extracted with ethyl acetate. The combined extracts are washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. The residue is taken up in 8 ml of DMF and stirred with 1.92 g (5.9 mmol) of cesium carbonate and 0.38 ml. (5.9 mmol) of methyl iodide for 3 hours at room temperature. The batch is mixed with 10% citric acid and extracted-with MTBE. The organic phase is washed with saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 250 mg of product.

Aufarbeitung

  1. extractionis extracted with ethyl acetate
  2. washThe combined extracts are washed with saturated NaCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated by evaporation in a vacuum
  5. washThe organic phase is washed with saturated NaCl
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by evaporation in a vacuum

Quellen und Nachweise

ORD-Eintrag
ord-831341dffb94456785663c930bfed1f1
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166592B2

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