Ethanol → Ethyl 3-bromo-4-fluorobenzoate

HRID 401789Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401789
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].S(Cl)(Cl)=O.[CH3:16][CH2:17]O>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([O:7][CH2:16][CH3:17])=[O:6]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 705093-Bromo-4-fluorobenzoic acid

Produkt 1

HCID 24770261Ethyl 3-bromo-4-fluorobenzoateAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of compound 3-bromo-4-fluoro-benzoic acid (430 g, 1.97 mol, 1 eq) in EtOH (2.3 L) was added dropwise thionyl chloride (287 mL, 3.94 mol, 2 eq) at 10° C. Then the mixture was heated to reflux overnight. The mixture was concentrated in vacuum to give a residue. The residue was dissolved in ethyl acetate (800 mL), washed with aqueous sodium hydrogen carbonate, brine (300 mL) and water (200 mL), then concentrated in vacuo to give title compound as a white solid (440 g, 1.78 mol, 90.3%).

Aufarbeitung

  1. temperatureThen the mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated in vacuum
  4. customto give a residue
  5. washwashed with aqueous sodium hydrogen carbonate, brine (300 mL) and water (200 mL)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-37187ffc81f7461590429120a506fa00
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741934B2

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