Boron tribromide → 2-Fluoro-4,5-dihydroxybenzaldehyde

HRID 468243

Reaktionsgleichung

Reaktionsgleichung von HRID 468243
[F:1][C:2]1[CH:9]=[C:8]([O:10]C)[C:7]([O:12]C)=[CH:6][C:3]=1[CH:4]=[O:5].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:9]=[C:8]([OH:10])[C:7]([OH:12])=[CH:6][C:3]=1[CH:4]=[O:5]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 6035952-Fluoro-4,5-dimethoxybenzaldehyde

Produkt 1

HCID 5933632-Fluoro-4,5-dihydroxybenzaldehydeAusbeute 314,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a stirred suspension of 2-fluoro-4,5-dimethoxy-benzaldehyde (3.00 g, 16.3 mmol) in dichloromethane (100 mL) was added BBr3 (12.2 mL, 130 mmol) dropwise at −78° C. under nitrogen atmosphere. After addition, the mixture was warmed to −30° C. and stirred at this temperature for 5 h. The reaction mixture was poured into ice water and the precipitated solid was collected by filtration and washed with dichloromethane to afford 2-fluoro-4,5-dihydroxy-benzaldehyde (8.0 g), which was used directly in the next step.

Aufarbeitung

  1. additionAfter addition
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-75f4d33c74344e3b87dff540107f8c06
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08623905B2

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