Boron tribromide → 3-Fluoro-4,5-dihydroxybenzaldehyde

HRID 39144

Reaktionsgleichung

Reaktionsgleichung von HRID 39144
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11]C)[C:9]=1[OH:10])[CH:5]=[O:6].B(Br)(Br)Br>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([OH:11])[C:9]=1[OH:10])[CH:5]=[O:6]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Produkt 1

HCID 5936643-Fluoro-4,5-dihydroxybenzaldehydeAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-30 °C

Versuchsvorschrift

To a suspension of 3-fluoro-4-hydroxy-5-methoxy-benzaldehyde (1.35 g, 7.94 mmol) in dichloromethane (100 mL) was added BBr3 (1.5 mL, 16 mmol) dropwise at −78° C. under N2. After addition, the mixture was warmed to −30° C. and it was stirred at this temperature for 5 h. The reaction mixture was poured into ice water. The precipitated solid was collected by filtration and washed with dichloromethane to afford 3-fluoro-4,5-dihydroxy-benzaldehyde (1.1 g, 89%), which was directly used 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-8469dc88f312436c81456e29da631f3e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524767B2

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