反应 #1509574

反应方程式

NaHCO3

Sodium azide

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

triflic anhydride

→

title compound

收率 44.1%

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

收率 44.1%

溶剂

DCM

反应条件

后处理

1. 1
   workup.STIRRINGstirred further overnight
2. 2
   其他the reaction
3. 3
   萃取the mixture extracted into EtOAc
4. 4
   其他The organic layer was separated
5. 5
   其他dried
6. 6
   浓缩concentrated in vacuum
7. 7
   其他the residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc)

实验过程

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).

来源