Reaktion #1509574

Reaktionsgleichung

NaHCO3

Sodium azide

3-bromo-N-methyl-5-nitro-benzamide

triflic anhydride

→

title compound

Ausbeute 44.1%

5-(3-Bromo-5-nitro-phenyl)-1-methyl-1H-tetrazole

Ausbeute 44.1%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred further overnight
2. 2
   Sonstigethe reaction
3. 3
   Extraktionthe mixture extracted into EtOAc
4. 4
   SonstigeThe organic layer was separated
5. 5
   Sonstigedried
6. 6
   Einengenconcentrated in vacuum
7. 7
   Sonstigethe residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc)

Vorschrift

To a solution of 3-bromo-N-methyl-5-nitro-benzamide (0.6 g) in DCM (15 ml) at −15° C. was added triflic anhydride (0.6 ml) and the reaction stirred for 30 min. Sodium azide (226 mg) was added and the reaction allowed to warm to room temperature and stirred further overnight. NaHCO3(aq) was added to neutralise the reaction and the mixture extracted into EtOAc. The organic layer was separated, dried and concentrated in vacuum and the residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc) to give the title compound (290 mg). Rf=0.51 (3:2 cyclohexane:EtOAc).

Quelle