Reacción #1509574

Ecuación de reacción

NaHCO3

Sodium azide

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

triflic anhydride

→

title compound

Rendimiento 44.1%

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

Rendimiento 44.1%

Disolventes

DCM

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirred further overnight
2. 2
   Otrothe reaction
3. 3
   Extracciónthe mixture extracted into EtOAc
4. 4
   OtroThe organic layer was separated
5. 5
   Otrodried
6. 6
   Concentraciónconcentrated in vacuum
7. 7
   Otrothe residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc)

Procedimiento

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).

Fuente