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Dimethylformamide → HCID 18677628, Verbindung

HRID 1634335
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1634335
Br[C:2]1[CH:3]=[C:4]([CH:10]2[O:15][CH2:14][CH2:13][CH2:12][O:11]2)[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1.[F:16][C:17]([F:25])([F:24])[C:18]([F:23])([F:22])C([O-])=O.[Na+].CN(C=O)C>[Cu]I.C1(C)C=CC=CC=1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:18]([F:23])([F:22])[C:17]([F:25])([F:24])[F:16])=[CH:3][C:4]=1[CH:10]1[O:15][CH2:14][CH2:13][CH2:12][O:11]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 6228DimethylformamideHCID 2733305Sodium pentafluoropropionateHCID 143787592-(5-Bromo-2-methoxyphenyl)-1,3-dioxane

Produkt 1

HCID 18677628HCID 18677628, VerbindungAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A 50 ml round bottom flask equipped with Dean-Stark trap and reflux condenser was charged with Compound 38 (1.0 g, 3.66 mmol), sodium pentafluoropropionate (1.29 g, 6.95 mmol) and copper(I) iodide (1.46 g, 7.69 mmol), DMF (15 ml) -toluene (6 ml). The slurry was heated to 120-140° C. (bath temperature) and toluene (6 ml) was removed by distillation. The reaction mixture was heated at 140° C. (inner temperature) for 15 h. The mixture was diluted with water (40 ml) —toluene (15 ml) —ethyl acetate (60 ml). The mixture was filtered through a pad of celite and the filter cake was washed with ethyl acetate. The filtrate was washed with water, and brine, dried(MgSO4) and concentrated in vacuo to give crude product. The crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(10:1-5:1) to give Compound 39 (1.07 g) as a pale yellow oil

Aufarbeitung

  1. customA 50 ml round bottom flask equipped with Dean-Stark trap
  2. temperaturereflux condenser
  3. customwas removed by distillation
  4. additionThe mixture was diluted with water (40 ml) —toluene (15 ml) —ethyl acetate (60 ml)
  5. filtrationThe mixture was filtered through a pad of celite
  6. washthe filter cake was washed with ethyl acetate
  7. washThe filtrate was washed with water, and brine, dried(MgSO4)
  8. concentrationconcentrated in vacuo
  9. customto give crude product
  10. customThe crude product was purified by column chromatography on silica gel with hexane-ethyl acetate(10:1-5:1)

Quellen und Nachweise

ORD-Eintrag
ord-56328f73a6b1450f9c0951654d6b513c
Quelldatensatz
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06506775B1

Notizen zur Reaktion

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