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

HRID 83703

Reaktionsgleichung

Reaktionsgleichung von HRID 83703
[Cl: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>[Cl: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 296223-Chloro-4-hydroxy-5-methoxybenzaldehyde

Produkt 1

HCID 24681823-Chloro-4,5-dihydroxybenzaldehydeAusbeute 105,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 3-chloro-4-hydroxy-5-methoxy-benzaldehyde (10 g, 54 mmol) in dichloromethane (300 mL) was added BBr3 (26.7 g, 107 mmol) dropwise at −40° C. under N2. After addition, the mixture was stirred at this temperature for 5 h and then was poured into ice water. The precipitated solid was filtered and washed with petroleum ether. The filtrate was evaporated under reduced pressure to afford 3-chloro-4,5-dihydroxybenzaldehyde (9.8 g, 89%), which was directly used in the next step.

Aufarbeitung

  1. additionAfter addition
  2. filtrationThe precipitated solid was filtered
  3. washwashed with petroleum ether
  4. customThe filtrate was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-84f89e65065d4550a32da904da12c408
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846753B2

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