Cesium carbonate → Methyl 3-(3-(((4-bromo-3-methylphenyl)methyl)oxy)phenyl)propanoate

HRID 1662310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662310
[OH:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][C:22]=1[CH3:29]>CN(C=O)C.O>[Br:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][O:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:5]=[CH:6][CH:7]=2)=[CH:23][C:22]=1[CH3:29]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 1512675Methyl 3-(3-hydroxyphenyl)propionateHCID 189606101-Bromo-4-(chloromethyl)-2-methylbenzene

Produkt 1

HCID 57705740Methyl 3-(3-(((4-bromo-3-methylphenyl)methyl)oxy)phenyl)propanoateAusbeute 90,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To flask containing methyl 3-(3-hydroxyphenyl)propanoate (available from Aagile Labs Division of Tyger Scientific) (0.25 g, 1.387 mmol) and cesium carbonate (0.5876 g, 1.804 mmol) in DMF (8 mL), was added 1.2 (0.3654 g, 1.665 mmol). The resulting mixture was then stirred overnight. The reaction was diluted with water and extracted with EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and then purified by combiflash (0 to 20% EtOAc/hexane) to provide 1.3 (0.4575 g, 90.78% yield). MS ESI (pos.) m/e: 382.0 (M+H2O)+.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by combiflash (0 to 20% EtOAc/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-ddb01c2074b141bda272d99f1161faa4
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030354B2

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