Dichloromethane → 2-Chloro-5-iodobenzaldehyde

HRID 602058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 602058
C(Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[CH2:12][OH:13].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>CCOCC>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[CH:7][C:6]=1[CH:12]=[O:13]

Komponenten

5

Edukt 3

HCID 6344DichloromethaneHCID 671539432-Chloro-5-iodobenzyl alcoholHCID 178418287HCID 178418287, Verbindung

Produkt 1

HCID 221152692-Chloro-5-iodobenzaldehydeAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A methylene chloride solution (99 mL) of (2-chloro-5-iodophenyl)methanol (9.01 g, 33.5 mmol) and PCC (8.67 g, 40.2 mmol) were combined and stirred at rt. After 16 h, Et2O was added and the solution stirred for 30 minutes. The solution was then filtered and the organic layer was washed with H2O (2×), NaHCO3 (3×), and brine. The organic layer was dried (Na2SO4), concentrated, and purified by Biotage chromatography (0%-20% EtOAc/hexanes) to afford 5.94 g of product (67%). 1H NMR (400 MHz, chloroform-d) δ ppm 10.38 (s, 1 H) 8.22 (d, J=2.02 Hz, 1 H) 7.83 (dd, J=8.46, 2.15 Hz, 1 H) 7.21 (d, J=8.59 Hz, 1 H).

Aufarbeitung

  1. stirringthe solution stirred for 30 minutes
  2. filtrationThe solution was then filtered
  3. washthe organic layer was washed with H2O (2×), NaHCO3 (3×), and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by Biotage chromatography (0%-20% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-212cfaf3c2f640db8ebeb4e873cca89c
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902394B2

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