Sodium Azide

Used Chemicals

• 4-Bromobenzonitrile [B1426]
• Sodium Azide [S0489]
• Triethylamine Hydrochloride (= Et₃N·HCl) [T0425]
• Toluene

Procedure

Sodium azide (139 mg, 2.14 mmol, 1.3 eq.) in toluene (3 mL) was added to a solution of 4-bromobenzonitrile (300 mg, 1.65 mmol) and triethylamine hydrochloride (295 mg, 2.14 mmol, 1.3 eq.) at room temperature. The mixture was stirred at 100 °C for 4 hours. Triethylamine hydrochloride (295 mg, 2.14 mmol, 1.3 eq.) and sodium azide (139 mg, 2.14 mmol, 1.3 eq.) were added and stirred overnight at the same temperature. Then the reaction mixture was quenched with water (15 mL) and the aqueous layer was washed with ethyl acetate (15 mL x 2) and was removed under reduced pressure and the residue was purified by column chromatography (on silica gel, dichloromethane:methanol = 5:1) and washed with acetonitrile:water (1:1, 6 mL) to give 5-(4-bromophenyl)-1H-tetrazole as a white solid (240 mg, 65% yield).

Experimenter’s Comments

The reaction mixture was monitored by UPLC.
The reaction was performed in a fume hood because hydrogen azide may be generated.

Analytical Data

5-(4-Bromophenyl)-1H-tetrazole

¹H NMR (400 MHz, CDCl₃); δ 7.99 (d, J = 8.0 Hz, 2H), 7.84 (d, J = 8.0 Hz, 2H).

Lead Reference

• (S)-5-PYRROLIDIN-2-YL-1H-TETRAZOLE
• V. Aureggi, V. Franckevicius, M. O. Kitching, S. V. Ley, D. A. Longbottom, A. J. Oelke, G. Sedelmeier, Org. Synth. 2008, 85, 72.

References

• Sodium Azide
  • K. Turnbull, B. Narsaiah, J. S. Yadav, T. Yakaiah, B. P. V. Lingaiah, e-EROS, 2007.