Reaktion #730217

Reaktionsgleichung

NaN3

1-(4-iodophenyl)-3-methyl-1H-pyrazole

NBS

AIBN

→

3-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole

Ausbeute 8.9%

Lösungsmittel

CCl4

EtOAc

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 5 hrs
3. 3
   Filtrationit was filtered
4. 4
   EinengenThe filtrate was concentrated in vacuo
5. 5
   workup.DISSOLUTIONThe residue was dissolved in DMF (8 mL)
6. 6
   SonstigeThe organic phase was separated
7. 7
   Trocknendried over Na2SO4
8. 8
   Einengenconcentrated in vacuo
9. 9
   SonstigeThe residue was purified by a silica gel column
10. 10
    Wascheneluted with hexane

Vorschrift

A mixture of 1-(4-iodophenyl)-3-methyl-1H-pyrazole (0.98 g, 3.45 mmol), NBS (0.80 g, 4.49 mmol) and AIBN (0.17 g, 1.03 mmol) in CCl4 (15 mL) was heated at reflux for 5 hrs. After being cooled to room temperature, it was filtered. The filtrate was concentrated in vacuo. The residue was dissolved in DMF (8 mL), NaN3 (0.400 g, 6.15 mmol) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column, eluted with hexane, then with 4-6% EtOAc in hexane to give 3-(azidomethyl)-1-(4-iodophenyl)-1H-pyrazole (0.10 g).

Quelle