Iodine → 1-(Benzyloxy)-2-iodo-4-(trifluoromethoxy)benzene

HRID 582471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582471
[I:1]I.[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(Cl)(Cl)Cl.ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]([F:19])([F:20])[F:21])=[CH:13][C:12]=1[I:1])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 2

HCID 807IodineHCID 215840942-Benzyloxy-5-(trifluoromethoxy)benzene

Produkt 1

HCID 113952781-(Benzyloxy)-2-iodo-4-(trifluoromethoxy)benzeneAusbeute 101,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 76299Silver trifluoroacetateKatalysatorHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Iodine (71.96 g, 0.28 mol) in chloroform was added dropwise to a mixture of 2-benzyloxy-5-(trifluoromethoxy)benzene (Preparation 12, 73.06 g, 0.27 mol) and silver trifluoroacetate (71.57 g, 0.32 mol) in dichloromethane and the mixture was stirred at room temperature for 18 hours. The mixture was filtered through celite, washed with aqueous sodium thiosulfate (5%, 2×2 l), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with hexane/ethyl acetate, to give the title compound as a colorless oil (108.03 g), containing 11% unreacted 2-benzyloxy-5-(trifluoromethoxy)iodobenzene. 1H NMR (360 MHz, CDCl3) δ 7.67 (1H, d, J=2.8 Hz), 7.40 (5H, m), 7.16 (1H, dd, J=8.9, 2.8 Hz), 6.82 (1H, d, J=8.9 Hz), and 5.14 (2H, s).

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. washwashed with aqueous sodium thiosulfate (5%, 2×2 l)
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluting with hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-534d4aff849e4b3686d4e558819d7d33
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925627

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