Dimethylformamide → (4-Bromophenylethynyl)trimethylsilane

HRID 726095

Reaktionsgleichung

Reaktionsgleichung von HRID 726095
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1I.CN(C)C=O.C(N(CC)CC)C.[CH3:21][Si:22]([C:25]#[CH:26])([CH3:24])[CH3:23]>[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[CH3:21][Si:22]([C:25]#[C:26][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:24])[CH3:23]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 114151-Bromo-2-iodobenzeneHCID 66111Trimethylsilylacetylene

Produkt 1

HCID 4226980(4-Bromophenylethynyl)trimethylsilaneAusbeute 105,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 150 g of 97% bromo iodo benzene, 500 ml of anhydrous dimethylformamide, 100 ml of triethylamine, 50 g of trimethylsilyl acetylene, 2.1 g of copper iodide and 2.22 g of bis-(triphenylphosphine)-palladium (II) dichloride was stirred for 2 hours and then 500 ml of ice-cooled water were added. The mixture was extracted 3 times with 500 ml of ethyl acetate and the organic phase was washed with salt water, then dried over sodium sulfate, and evaporated under reduced pressure to obtain 136.542 g of a brown oil which was purified by distillation under reduced pressure to obtain 106.979 g of the expected product with a boiling point of 75°-82° C. under 0.2 mbar and a melting point of 62° C.

Aufarbeitung

  1. additionwere added
  2. extractionThe mixture was extracted 3 times with 500 ml of ethyl acetate
  3. washthe organic phase was washed with salt water
  4. dry with materialdried over sodium sulfate
  5. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-020795ec5693400798a1ee4408a40f81
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05707982

Verknüpfte Notizen

Wird geladen…