(3-Bromo-4-chlorophenyl)methanol → 3-Bromo-4-chlorobenzaldehyde

HRID 488842Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488842
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][OH:6].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH:5]=[O:6]

Komponenten

4

Edukt 2

HCID 50998689(3-Bromo-4-chlorophenyl)methanolHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 140498093-Bromo-4-chlorobenzaldehydeAusbeute 93,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-4-chlorobenzyl alcohol (2.73 g, 12.34 mmol) in dichloromethane (75 mL) was added, at room temperature, pyridinium chlorochromate (2.66 g, 12.34 mmol). The reaction mixture was stirred at room temperature for 1 hr then filtered over celite. The solvent was removed under reduced pressure and the residue chromatographed on silica gel (10% ethyl acetate in hexane) to afford 2.52 g of 3-bromo-4-chloro-benzaldehyde (93% yield). 1H NMR (300 MHz; CDCl3) 1H NMR (300 MHz; CDCl3) 7.65 (d, J=8.1 Hz, 1H); 7.78 (dd, J1=8.4 Hz, J2=2.1 Hz, 1H); 8.12 (d, J=2.1 Hz, 1H).

Aufarbeitung

  1. filtrationthen filtered over celite
  2. customThe solvent was removed under reduced pressure
  3. customthe residue chromatographed on silica gel (10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-cb523b4e75e34adab75b6ed62a0175ed
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06974826B2

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