2,4,6-Triiodophenol → (2,4,6-Triiodophenyl)-2,2,3,4,4-pentafluoro-3,4-dibromo-butyrate

HRID 6311

Reaktionsgleichung

Reaktionsgleichung von HRID 6311
[CH:1]1[C:2]([I:10])=[CH:3][C:4]([I:9])=[C:5]([OH:8])[C:6]=1[I:7].[F:11][C:12]([F:23])([C:16]([F:22])([Br:21])[C:17]([F:20])([F:19])[Br:18])[C:13](Cl)=[O:14]>N1C=CC=CC=1>[I:7][C:6]1[CH:1]=[C:2]([I:10])[CH:3]=[C:4]([I:9])[C:5]=1[O:8][C:13](=[O:14])[C:12]([F:11])([F:23])[C:16]([F:22])([Br:21])[C:17]([F:20])([F:19])[Br:18]

Komponenten

4

Edukt 2

HCID 118622,4,6-TriiodophenolHCID 145335373,4-Dibromo-2,2,3,4,4-pentafluorobutanoyl chloride

Produkt 1

HCID 14533541(2,4,6-Triiodophenyl)-2,2,3,4,4-pentafluoro-3,4-dibromo-butyrateAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

100 grams of triiodophenol were dissolved in 100 ml of pyridine with warming to 50° C. 75 grams of 2,2,3,4,4-pentafluoro-3,4-dibromo-butyryl chloride were added dropwise through a dropping funnel with stirring at such a rate that the temperature did not rise above 65° C. The mixture was stirred at 50° C. for an additional 30 minutes, then overnight at room temperature. The mixture was washed in a separatory funnel three times with 500 ml of DI water, then filtered through a column of silica and the solvent evaporated. The material was then chromatographed on a column of silica using FREON 113 (trichlorotrifluroethane) as eluent. Chromatography on silica gave 75.5 grams of material 99% pure. The material solidified at room temperature and has a melting point of 50° C. I.R.(ν, in cm-1)=3050, 3090 (Ar--H); 1800 (C=O); 1570, 1415 (Ar C=C). m/e 62 (47%, C5H2); 69 (18%, CF3); 129 (22%, CF2Br); 131 (70%, CF2Br and C3F5); 189 (60%, C5H2I); 344 (56%, C6H2I2O); 471 (100%, C6H2I3O).

Aufarbeitung

  1. customdid not rise above 65° C
  2. stirringThe mixture was stirred at 50° C. for an additional 30 minutes
  3. customovernight
  4. customat room temperature
  5. washThe mixture was washed in a separatory funnel three times with 500 ml of DI water
  6. filtrationfiltered through a column of silica
  7. customthe solvent evaporated
  8. customThe material was then chromatographed on a column of silica using FREON 113 (trichlorotrifluroethane) as eluent

Quellen und Nachweise

ORD-Eintrag
ord-6ff4bdd1e3964baaae33d90c3af4eb2c
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248432

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