Triethylamine → (3-Ethyl-4-fluoro-phenylethynyl)-trimethyl-silane

HRID 2415257Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415257
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.[CH3:11][Si:12]([C:15]#[CH:16])([CH3:14])[CH3:13].[Li+].[Cl-].C(N(CC)CC)C>CN(C)C=O.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.O>[CH2:9]([C:4]1[CH:3]=[C:2]([C:16]#[C:15][Si:12]([CH3:14])([CH3:13])[CH3:11])[CH:7]=[CH:6][C:5]=1[F:8])[CH3:10]

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 433294Lithium ChlorideHCID 226410254-Bromo-2-ethyl-1-fluorobenzene

Produkt 1

HCID 22641049(3-Ethyl-4-fluoro-phenylethynyl)-trimethyl-silane

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 4-bromo-2-ethyl-1-fluoro-benzene (2.4 g, 11.82 mmol) in N,N-dimethylformamide (100 mL), trimethylsilyl acetylene (2.0 mL, 14.19 mmol), PdCl2(PPh3)2 (500 mg, 0.72 mmol), LiCl (1 g, 23.64 mmol), CuI (25 mg, 0.1 mmol) and triethylamine (3 mL) were added and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was poured into water and extracted with diethyl ether. The extract was dried (Na2SO4) and concentrated. The residue was chromatographed on silica gel (hexanes) to give a brown oil. 1.58 g, 61%.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. dry with materialThe extract was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel (hexanes)
  5. customto give a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-3abf9204343a4dd98c599d4fb9400c59
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06818663B2

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