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

HRID 1270062Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270062
[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-dichlorophenylethynyl)-trimethyl-silane 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-43a37e7ba6764aafb1faec62b5538ce9
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202213B2

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