Dimethylformamide → (4-Bromophenylethynyl)trimethylsilane

HRID 486312

Reaktionsgleichung

Reaktionsgleichung von HRID 486312
[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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd](Cl)Cl.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 13169693Triphenylphosphine palladium dichlorideKatalysatorHCID 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-03e6a71e8cec49c0b455f5e5760b9254
Quelldatensatz
uspto-grants-1994_03
Patentnummer
US05290771

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