Potassium Iodide → 3,5-Dichloro-4-(3-ethinylpropoxy)benzonitrile
Reaktionsgleichung
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[OH:10])[C:5]#[N:6].Cl[CH2:13][CH2:14][CH2:15][C:16]#[CH:17].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN1CCCC1=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[O:10][CH2:17][CH2:16][CH2:15][C:14]#[CH:13])[C:5]#[N:6]Komponenten
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A mixture of 10.0 g 3,5-dichloro-4-hydroxybenzonitrile, 6.2 mls 5-chloro-1-pentyne, 18.38 g milled potassium carbonate (100%) and 0.88 g potassium iodide in 125 mls N-methylpyrrolidone was heated at 60° C. with stirring overnight. An additional 4.6 g milled potassium carbonate and 2.82 mls 5-chloro-1-pentyne was added and heating was continued for two days. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extracts were washed with aqueous 10% potassium bisulfate solution, water and saturated sodium chloride solution, dried (MgSO4) and concentrated in vacuo. The resulting oily residue was subjected to flash chromatography (silica gel; 10:90 ethyl acetate/hexane) to yield 7.03 g of the title compound.
Aufarbeitung
- additionwas added
- temperatureheating
- waitwas continued for two days
- extractionextracted with ethyl acetate
- washThe ethyl acetate extracts were washed with aqueous 10% potassium bisulfate solution, water and saturated sodium chloride solution
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-d54b349e53d04c5784b1f250650fd085
- Quelldatensatz
- uspto-grants-1992_12
- Patentnummer
- US05175177
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