3-Bromobiphenyl → [([1,1'-Biphenyl]-3-yl)ethynyl](trimethyl)silane

HRID 271108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271108
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[C:14]([Si:16]([CH3:19])([CH3:18])[CH3:17])#[CH:15]>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.[Cu](I)I>[C:4]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=[C:2]([C:15]#[C:14][Si:16]([CH3:19])([CH3:18])[CH3:17])[CH:3]=1

Komponenten

5

Edukt 2

HCID 164493-BromobiphenylHCID 66111Trimethylsilylacetylene

Produkt 1

HCID 59834575[([1,1'-Biphenyl]-3-yl)ethynyl](trimethyl)silaneAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysator

Versuchsvorschrift

To a solution of 3-bromo-1,1′-biphenyl (5.06 g, 21.76 mmol) in TEA (20 mL) are added dichlorobis(triphenylphosphine)palladium (0.47 g, 0.65 mmol), copper iodide (0.08 g, 0.44 mmol) and ethynyl(trimethyl)silane (4.62 mL, 32.64 mmol). The reaction mixture is refluxed for 3 h and cooled to room temperature. After evaporation of the solvent, the crude material is purified by chromatography (silica gel, 100% hexane) to afford the title compound (4.81 g, 88%) as an oil. MS (+) EI: 250 M+.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 3 h
  2. customAfter evaporation of the solvent
  3. customthe crude material is purified by chromatography (silica gel, 100% hexane)

Quellen und Nachweise

ORD-Eintrag
ord-65c875ef60d8490dbfbe4e5a2ace50f6
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452885B2

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