Reaktion #53209

Reaktionsgleichung

propargyl alcohol

triethylamine

4-bromonitrobenzene

→

4-(3-hydroxyprop-1-ynyl)-nitrobenzene

Lösungsmittel

acetonitrile

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenIt is washed with water and ammonia water
2. 2
   Filtrationfiltered through Celite
3. 3
   SonstigeThe product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1)

Vorschrift

8.55 g (0.15 mol) of propargyl alcohol and 152 ml (110 g, 1.09 mol) of triethylamine are added to a solution of 20.2 g (0.1 mol) of 4-bromonitrobenzene in 285 ml of acetonitrile. The reaction solution is heated to 100° C. 11.9 g (10 mmol) of Pd(Pph3)4 and 3.94 g (20 mmol) of copper (I) iodide are added. After 10 minutes the solvent is eliminated in vacuo and the residue taken up in ethyl acetate. It is washed with water and ammonia water, filtered through Celite and the solvent is eliminated in vacuo. The product is obtained by chromatography on silica gel (dichloromethane/methanol=10:1).

Quelle