Aniline → Azidobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of aniline (300 mg, 3.22 mmol) in water (2 mL) and conc. HCl (1 mL) at 0° C. was slowly added a solution of sodium nitrite (289 mg, 4.19 mmol) in water (1 mL). The reaction mixture was stirred at 0° C. for 10 min then a solution of sodium azide (251 mg, 3.87 mmol) in water (1 mL) was slowly added. The reaction mixture was stirred at room temp for 1 h then extracted with Et2O (2×). The combined organics were washed with water, dried over MgSO4, and carefully concentrated at 300 torr and ambient temperature to afford 350 mg (91%) of azidobenzene as a light orange oil.

Provenance & Evidence