Reaktion #1447128

Reaktionsgleichung

ortho-bromoacetanilide

3,3-dimethyl-1-butyne

water

→

N-[2-(3,3-dimethylbut-1-ynyl)-phenyl]acetamide

Ausbeute 100.3%

Lösungsmittel

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted 3 times with in each case 250 ml of diethyl ether
2. 2
   Trocknenthe extracts were dried over sodium sulphate
3. 3
   Einengenconcentrated
4. 4
   SonstigeColumn-chromatographic purification on silica gel 60 with methylene chloride

Vorschrift

Under argon, 25.7 g (120 mmol) of ortho-bromoacetanilide, 5.05 g (7.2 mmol) of bis(triphenylphosphine)palladium(II) chloride and 1.37 g (7.2 mmol) of copper(I) iodide were initially charged in 450 ml of triethylamine. At room temperature, 17.8 g (180 mmol) of 3,3-dimethyl-1-butyne were then added dropwise over a period of 10 min, and the mixture is stirred at 50° C. for 5 h. The reaction mixture was poured into 2 l of water and extracted 3 times with in each case 250 ml of diethyl ether, and the extracts were dried over sodium sulphate and concentrated. Column-chromatographic purification on silica gel 60 with methylene chloride gave 25.9 g of N-[2-(3,3-dimethylbut-1-ynyl)-phenyl]acetamide of logP (pH 2.3)=3.03.

Quelle