Potassium Carbonate → 2-(2,4,6-Triiodophenoxy)nonane

HRID 1728283

Reaktionsgleichung

Reaktionsgleichung von HRID 1728283
CS(OC(CCCCCCC)C)(=O)=O.C1C(I)=CC(I)=C(O)C=1I.C(=O)([O-])[O-].[K+].[K+].[I:31][C:32]1[CH:53]=[C:52]([I:54])[CH:51]=[C:50]([I:55])[C:33]=1[O:34][CH:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]CCCCCC)[CH3:36]>CN(C=O)C>[I:31][C:32]1[CH:53]=[C:52]([I:54])[CH:51]=[C:50]([I:55])[C:33]=1[O:34][CH:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH3:36]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 118622,4,6-TriiodophenolHCID 149160062-MethanesulfonyloxynonaneHCID 153433092-(2,4,6-Triiodophenoxy)pentadecane2×

Produkt 1

HCID 153433132-(2,4,6-Triiodophenoxy)nonaneAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The 2-methanesulfonyloxynonane (22.8 g, 102 mmol), triiodophenol (48.8 g, 103 mmol) and potassium carbonate (14.2 g, 103 mmol) were reacted in DMF (206 ml) as per 2-(2,4,6-triiodophenoxy)pentadecane except at an oil bath temperature of 82° C. for 14 hrs. The reaction was processed as for 2-(2,4,6-triiodophenoxy)pentadecane to provide a light brown oil. Flash column chromatography (silica, hexanes) provided 2-(2,4,6-triiodophenoxy)nonane (40.8 g, 68.0%). Title Compound: 1H (300 MHz) and 13C (75 MHz) NMR spectra were consistent with the desired structure. Calculated for C15H21I3O: C, 30.13; H, 3.54; I, 63.66. Found: C, 30.52, H, 3.49; I, 63.47.

Aufarbeitung

  1. customto provide a light brown oil

Quellen und Nachweise

ORD-Eintrag
ord-cabdedf8ecdf43839a2ce3a0910081fb
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05326553

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