4-Iodoaniline → 4-[(4-Hexylphenyl)ethynyl]aniline

HRID 551977Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551977
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:13][CH:12]=1)#[CH:10]>C(#N)C.[Cu]I.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>[CH2:17]([C:14]1[CH:13]=[CH:12][C:11]([C:9]#[C:10][C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)=[CH:16][CH:15]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Komponenten

6

Edukt 2

HCID 108934-IodoanilineHCID 27751291-Ethynyl-4-hexylbenzene

Produkt 1

HCID 575545514-[(4-Hexylphenyl)ethynyl]anilineAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a stirred solution of 4-iodoaniline (10.0 g, 45.6 mmol, Aldrich) and 1-eth-1-ynyl-4-hexylbenzene (10.0 g, 53.0 mol, Maybridge) in anhydrous acetonitrile (200 mL) under nitrogen was added CuI (0.43 g, 2.2 mmol), TEA (14.0 g, 138 mmol) followed by Pd(PPh3)2Cl2 (1.6 g, 2.2 mmol). The reaction mixture was stirred at 85° C. for 22 hours. The solvent was removed under reduced pressure. The residue was diluted with Et2O (200 mL) 20 and washed with water and brine. The organic layer was dried (MgSO4) and the solvent was removed under reduced pressure. The crude product was purified by chromatography Wet ether/EtOAc 4/1) to give 11.0 g (87%) of the title compound as a pale yellow solid. TLC-Pet ether/EtOAc (4/1): Rf=0.4. HPLC purity >98%.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with Et2O (200 mL) 20
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was purified by chromatography Wet ether/EtOAc 4/1)

Quellen und Nachweise

ORD-Eintrag
ord-9c9072e573fc449a8c19e24ce6f8155e
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947851B2

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