반응 #1552094

반응 방정식

3-iodoaniline

3,3-dimethyl-1-butyne

water

→

crude product

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

용매

triethylamine

반응 조건

후처리

1. 1
   온도With ice-cooling
2. 2
   기타remains at 20° C
3. 3
   workup.ADDITIONAfter the addition
4. 4
   농축The reaction solution is concentrated under reduced pressure
5. 5
   기타the residue formed
6. 6
   추출The mixture is then extracted three times with diethyl ether
7. 7
   세척The combined organic phases are once more washed with water
8. 8
   건조dried with sodium sulphate
9. 9
   농축concentrated under reduced pressure

실험 절차

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.

출처