Imidazole → 1,4-Dichloro-2-(5-iodopent-1-ynyl)benzene

HRID 395383

Reaktionsgleichung

Reaktionsgleichung von HRID 395383
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]#[C:10][CH2:11][CH2:12][CH2:13]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:39]I>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]#[C:10][CH2:11][CH2:12][CH2:13][I:39]

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 223207595-(2,5-Dichlorophenyl)pent-4-yn-1-ol

Produkt 1

HCID 129889421,4-Dichloro-2-(5-iodopent-1-ynyl)benzeneAusbeute 72,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

5-(2,5-Dichlorophenyl)pent-4-yn-1-ol (13.7 g, 59.8 mmol), triphenylphosphine (20.4 g, 77.8 mmol), and imidazole (5.71 g, 83.8 mmol) in a mixed solvent (100 ml acetonitrile-150 ml ether) was stirred under nitrogen at 0° C., and to this was slowly added iodine (21.3 g, 83.8 mmol). The solution was allowed to warm to room temperature and stirring was continued for 18 hours. This was chromatographed on silica gel with hexane to give the title compound (14.7 g, 72%), MS m/z 337.9 (M−H calcd. for C11H9Cl2I=338.0).

Aufarbeitung

  1. customThis was chromatographed on silica gel with hexane

Quellen und Nachweise

ORD-Eintrag
ord-6749d3ecd3f24a1ebce3e3d2ad31d8e4
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06605628B1

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