Реакция #1728795

Уравнение реакции

Water

5-(4-cyanophenoxy)-1-hydroxy-2,1-benzoxaborole

sodium azide

ammonium chloride

→

compound

Выход 23.5%

5-(4-(1H-tetrazol-5-yl)phenoxy)benzo[c][1,2]oxaborol-1(3H)-ol

Выход 23.5%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Экстракцияthe mixture was extracted with ethyl acetate
2. 2
   ПромывкаThe organic layer was washed with water and brine
3. 3
   Сушкаdried on anhydrous sodium sulfate
4. 4
   ДругоеThe solvent was removed under reduced pressure
5. 5
   Другоеthe residue was purified by silica gel column chromatography (ethyl acetate)

Методика

A mixture of 5-(4-cyanophenoxy)-1-hydroxy-2,1-benzoxaborole (200 mg, 0.797 mmol), sodium azide (103 mg, 1.59 mmol), and ammonium chloride (85 mg, 1.6 mmol) in N,N-dimethylformamide (5 mL) was stirred at 80° C. for two days. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate) followed by trituration with ethyl acetate to give the target compound (55 mg, 23%).

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