Reaction #2006467

Reaction equation

Water

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

sodium azide

ammonium chloride

N,N-dimethylformamide

→

compound

Yield 23.0%

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

Yield 23.0%

Conditions

Workup

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

Procedure

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