反応 #1509574

反応方程式

NaHCO3

Sodium azide

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

triflic anhydride

→

title compound

収率 44.1%

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

収率 44.1%

溶媒

DCM

反応条件

後処理

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

実験手順

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).

出典