Phenol, 3-bromo-2,4,6-triiodo- → (2,4,6-Triiodo-3-bromo-phenyl)-2,2,3,4,4-pentafluoro-3,4-dibromobutyrate

HRID 6312

Reaktionsgleichung

Reaktionsgleichung von HRID 6312
[Br:1][C:2]1[C:3]([I:11])=[C:4]([OH:10])[C:5]([I:9])=[CH:6][C:7]=1[I:8].[F:12][C:13]([F:24])([C:17]([F:23])([Br:22])[C:18]([F:21])([F:20])[Br:19])[C:14](Cl)=[O:15]>N1C=CC=CC=1>[I:11][C:3]1[C:2]([Br:1])=[C:7]([I:8])[CH:6]=[C:5]([I:9])[C:4]=1[O:10][C:14](=[O:15])[C:13]([F:12])([F:24])[C:17]([F:23])([Br:22])[C:18]([F:21])([F:20])[Br:19]

Komponenten

4

Edukt 2

HCID 10218345Phenol, 3-bromo-2,4,6-triiodo-HCID 145335373,4-Dibromo-2,2,3,4,4-pentafluorobutanoyl chloride

Produkt 1

HCID 14533542(2,4,6-Triiodo-3-bromo-phenyl)-2,2,3,4,4-pentafluoro-3,4-dibromobutyrate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

20.3 grams of 3-bromo-2,4,6-triiodophenol (m.p 155°-157° C.) were dissolved in 50 ml of pyridine 13.0 grams of 2,2,3,4,4-pentafluoro-3,4-dibromo-butyryl chloride were added dropwise through a dropping funnel with stirring. The mixture was stirred overnight at room temperature. The mixture was washed in a separatory funnel twice with 250 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. The sample (25 grams), which slowly crystallized at room temperature, was shown to be pure ester (97%) by gc/ms. It is suitable for use as a fluid above its melting point of 56°-57° C. m/e (chemical ionization) 129 (21%, CF2Br); 131 (100%, CF2Br and C3F5); 140 (13%, C5HBr); 142 (13%, C5HBr); 188 (14%, C5HI); 267, 269 (11%, 10% C5BrIH); 315 (4%, C5I2H); 422, 424 (6%, 7%, C6I2HBrO); 549, 551 (5%, 4%, C6I3HBrO); 866, 868, 870, 872 (0.2%, 0.6%, 0.4%, 0.2%, molecular ion). I.R.(ν, in cm-1) =3080 (Ar--H); 1800 (C=O); 1550, 1520 (Ar C=C).

Aufarbeitung

  1. additionwere added dropwise through a dropping funnel
  2. stirringThe mixture was stirred overnight at room temperature
  3. washThe mixture was washed in a separatory funnel twice with 250 ml of DI water
  4. filtrationfiltered through a column of silica
  5. customthe solvent evaporated
  6. customThe material was then chromatographed on a column of silica using FREON 113 (trichlorotrifluroethane) as eluent
  7. customThe sample (25 grams), which slowly crystallized at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-af04e3fc60fd4e9a9acc5f15ce50eda6
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05248432

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