Réaction #1552094

Équation de réaction

3-iodoaniline

3,3-dimethyl-1-butyne

water

→

crude product

3-(3,3-dimethylbut-1-yn-1-yl)aniline

Solvants

triethylamine

Conditions de réaction

Traitement

1. 1
   TempératureWith ice-cooling
2. 2
   Autreremains at 20° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   ConcentrationThe reaction solution is concentrated under reduced pressure
5. 5
   Autrethe residue formed
6. 6
   ExtractionThe mixture is then extracted three times with diethyl ether
7. 7
   LavageThe combined organic phases are once more washed with water
8. 8
   Séchagedried with sodium sulphate
9. 9
   Concentrationconcentrated under reduced pressure

Mode opératoire

1.05 g (1.5 mmol) of bis(triphenylphosphine)palladium(II) chloride and 0.26 g (1.5 mmol) of copper(I) iodide are added to a solution consisting of 5.47 g (25 mmol) of 3-iodoaniline in 40 ml of triethylamine. With ice-cooling, 3.08 g (37.5 mmol) of 3,3-dimethyl-1-butyne are added dropwise such that the temperature remains at 20° C. After the addition has ended, the mixture is stirred at 20° C. for 20 hours. The reaction solution is concentrated under reduced pressure and the residue formed is stirred into 1 l of water. The mixture is then extracted three times with diethyl ether. The combined organic phases are once more washed with water, dried with sodium sulphate and concentrated under reduced pressure. The crude product obtained is purified by silica gel chromatography (mobile phase methylene chloride). This gives 2.70 g (60% of theory) of 3-(3,3-dimethylbut-1-yn-1-yl)aniline having a content of 97% according to HPLC. log P=2.71.

Source