Réaction #2006467

Équation de réaction

Water

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

sodium azide

ammonium chloride

N,N-dimethylformamide

→

compound

Rendement 23.0%

1-Hydroxy-5-[4-(tetrazole-1-yl)phenoxy]-2,1-benzoxaborole

Rendement 23.0%

Conditions de réaction

Traitement

1. 1
   Extractionthe mixture was extracted with ethyl acetate
2. 2
   LavageThe organic layer was washed with water and brine
3. 3
   Séchagedried on anhydrous sodium sulfate
4. 4
   AutreThe solvent was removed under reduced pressure
5. 5
   Autrethe residue was purified by silica gel column chromatography (ethyl acetate)

Mode opératoire

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%).

Source