Iodine → 3-iodo-4-methoxybenzaldehyde

HRID 1360989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360989
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[I:11]I>ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[I:11][C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:3]=1[O:2][CH3:1])[CH:7]=[O:8]

Komponenten

5

Edukt 2

HCID 807IodineHCID 312444-Methoxybenzaldehyde

Produkt 1

HCID 14943763-iodo-4-methoxybenzaldehydeAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76299Silver trifluoroacetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

4-Methoxybenzaldehyde (0.5 g, 3.67 mmol) and silver trifluoroacetate (0.92 g, 4.19 mmol) were mixed in dichloromethane (25 mL). Iodine (1.19 g, 4.7 mmol) was added in small portions and the mixture was stirred overnight at room temperature under nitrogen. The mixture was subsequently filtered and the residue washed with DCM. The combined filtrates were treated with an aqueous sodium thiosulfate solution (1 M) until the colour disappeared. Subsequent extraction with dichloromethane (3×20 mL) followed by drying with MgSO4 and evaporation in vacuo afforded 0.94 g of 3-iodo-4-methoxybenzaldehyde.

Aufarbeitung

  1. filtrationThe mixture was subsequently filtered
  2. washthe residue washed with DCM
  3. additionThe combined filtrates were treated with an aqueous sodium thiosulfate solution (1 M) until the colour
  4. extractionSubsequent extraction with dichloromethane (3×20 mL)
  5. dry with materialby drying with MgSO4 and evaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-16111e0dcf994cf784ac2dd84382a8a5
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879893B2

Notizen zur Reaktion

Wird geladen…