Réaction #1509574

Équation de réaction

NaHCO3

Sodium azide

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

triflic anhydride

→

title compound

Rendement 44.1%

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

Rendement 44.1%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGstirred further overnight
2. 2
   Autrethe reaction
3. 3
   Extractionthe mixture extracted into EtOAc
4. 4
   AutreThe organic layer was separated
5. 5
   Autredried
6. 6
   Concentrationconcentrated in vacuum
7. 7
   Autrethe residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc)

Mode opératoire

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).

Source