Potassium Carbonate → Ethyl 3-(2-hydroxy-2-methylpropoxy)-4-bromobenzoate

HRID 2102893Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2102893
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[OH:13].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:21][C:22]([CH3:25])([OH:24])[CH3:23]>CN(C=O)C>[OH:24][C:22]([CH3:25])([CH3:23])[CH2:21][O:13][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:2]=1[Br:1])[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 684091-Chloro-2-methylpropan-2-olHCID 12134897Ethyl 4-bromo-3-hydroxybenzoate

Produkt 1

HCID 57804223Ethyl 3-(2-hydroxy-2-methylpropoxy)-4-bromobenzoateAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Ethyl 4-bromo-3-hydroxybenzoate (1.5 g, 6.12 mmol), potassium carbonate (5.07 g, 36.72 mmol) and 1-chloro-2-methylpropan-2-ol (0.75 mL, 7.34 mmol) were placed in 50 mL DMF and the reaction was heated at 80° C. for 18 h. The mixture was cooled and partitioned between EtOAc and water. The organic layer was separated, washed with water, brine, dried (Na2SO4), filtered, and the filtrate was concentrated under vacuum to an oil. Purification by column chromatography on silica gel using EtOAc/hexane (0-50%) gave the product (0.5 g, 26%) as a yellow oil.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompartitioned between EtOAc and water
  3. customThe organic layer was separated
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under vacuum to an oil
  8. customPurification by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5398f02845a54f9caff94ec8944468e3
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576099B2

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