Реакция #1509574

Уравнение реакции

NaHCO3

Sodium azide

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

triflic anhydride

→

title compound

Выход 44.1%

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

Выход 44.1%

Растворители

DCM

Условия реакции

Обработка

1. 1
   workup.STIRRINGstirred further overnight
2. 2
   Другоеthe reaction
3. 3
   Экстракцияthe mixture extracted into EtOAc
4. 4
   ДругоеThe organic layer was separated
5. 5
   Другоеdried
6. 6
   Концентрированиеconcentrated in vacuum
7. 7
   Другоеthe residue purified by flash chromatography (9:1 to 2:8 cyclohexane:EtOAc)

Методика

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).

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