Trimethylsilylacetylene → [2-(3,5-Dichlorophenyl)ethynyl]trimethylsilane

HRID 413938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413938
[Cl:1][C:2]1[CH:7]=[C:6](I)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>C(NCC)C.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>[Cl:1][C:2]1[CH:7]=[C:6]([C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10])[CH:5]=[C:4]([Cl:9])[CH:3]=1

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 764241,3-Dichloro-5-iodobenzene

Produkt 1

HCID 22570337[2-(3,5-Dichlorophenyl)ethynyl]trimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

To a solution of 1,3-dichloro-5-iodo-benzene (5.44 g, 20 mmol) in diethylamine (75 mL) was added PdCl2(PPh3)2 (280 mg, 0.4 mmol), trimethylsilylacetylene (2.36 g, 24.0 mmol) and copper(I)iodide (20 mg, 0.1 mmol). The reaction mixture was stirred at room temperature for 24 h, filtered and evaporated. The residue was purified by column chromatography using heptane:ethyl acetate (8:2) as eluent. The desired (3,5-dichloro-phenylethynyl)-trimethylsilane product was isolated in 4.85 g yield.

Aufarbeitung

  1. filtrationfiltered
  2. customevaporated
  3. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-061369dd3e2d4ce58ce9ce7d9fca3fbb
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06569901B2

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