Reaction #1509574

Reaction equation

NaHCO3

Sodium azide

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

triflic anhydride

→

title compound

Yield 44.1%

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

Yield 44.1%

Solvents

DCM

Conditions

Workup

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

Procedure

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