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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 271729Erstellt: 26. Oktober 2026

Triethylamine → (4-Bromo-thiophen-2-ylethynyl)-trimethyl-silane

https://huagongshe.com/reaction/271729

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriethylamineHCID 8471—
EduktTrimethylsilylacetyleneHCID 66111—
EduktThiophene, 2,4-dibromo-HCID 2724560—
KatalysatorCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt(4-Bromo-thiophen-2-ylethynyl)-trimethyl-silaneHCID 67364285—

Reaktionsbedingungen

Temperatur-78 °C

Reaktionsschritte

Under an argon atmosphere 0.37 g (1.94 mmol) CuI, 2.24 g (1.94 mmol) tetrakis-triphenylphosphane-palladium and 16.2 mL triethylamine are added to a solution of 10.0 g (38.85 mmol) 2,4-dibromothiophene in 300 mL THF, the reaction mixture is cooled to −78° C. and then at this temperature a solution of 5.6 mL (38.85 mmol) ethynyl-trimethyl-silane in 250 mL THF is slowly added dropwise. After the addition has ended the mixture is allowed to heat up slowly to RT and stirred overnight. The mixture is evaporated down i.vac., the residue is combined with water, extracted exhaustively with DCM and the combined organic phases are dried over MgSO4. After the desiccant and solvent have been eliminated the residue is triturated with PE, filtered to remove insoluble ingredients and the solvent is evaporated down. The residue is purified by chromatography (silica gel, PE).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS07452911B2
Quelldatensatzuspto-grants-2008_11
ORD IDord-c8b60b39523b4910834b0eeac7c0c3b7
Quellennotizuspto-grants-2008_11