Sodium Carbonate → 2-Benzyloxy propoxy-2-bromobenzaldehyde

HRID 1160074Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160074
[Br:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C([O-])([O-])=O.[Na+].[Na+].[CH2:17]([O:24][CH:25]([CH3:28])[CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CS(C)=O.O>[CH2:17]([O:24][CH:25]([CH3:28])[CH2:26][O:27][C:9]1[C:2]([Br:1])=[C:3]([CH:6]=[CH:7][CH:8]=1)[CH:4]=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 5618252-(Benzyloxy)propan-1-olHCID 27733192-Bromo-4-fluorobenzaldehyde

Produkt 1

HCID 866341472-Benzyloxy propoxy-2-bromobenzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 2-bromo-4-fluoro-benzaldehyde (30.0 g, 148 mmol), Na2CO3 (78.31 g, 738.8 mmol) and 2-benzyloxy propanol (24.56 g, 147.8 mmol) in anhydrous DMSO (300 mL) was heated with stirring at 130° C. (bath temp) for 72 h under N2. The reaction mixture was cooled to rt and diluted with H2O and extracted with EtOAc. The organic layer was washed with H2O then brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (hexane to 30% EtOAc in hexane) to give the title compound: yield 3.84 g (7%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureThe reaction mixture was cooled to rt
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with H2O
  5. dry with materialbrine, dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (hexane to 30% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-1f84421ea478457c98600ec826e27278
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816344B2

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