Hydrochloric Acid → 2-Azido-1,3-dichloro-benzene

Participants

Reaction Steps

To a 0° C. solution of 2,6-dichloroaniline (2.00 g) in ethyl acetate (40 mL) is added concentrated hydrochloric acid (12 mL). The reaction is stirred for 10 minutes. To this solution is added a solution of sodium nitrite (2.55 g) in water (7.5 mL) over 3 minutes. Upon completion of the addition, the reaction is stirred for an additional 30 minutes. A solution of sodium azide (2.41 g) in water (8 mL) is added over 5 minutes. After 30 minutes, pH 7 buffer (50 mL) is added and the reaction is transferred to a separatory funnel. The layers are separated and the aqueous layer is extracted with ethyl acetate. The organic layers are combined and washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound (2.11 g). 1H NMR (400 MHz, CDCl3) δ 7.3-7.27 (d, 2H), 7.07-7.02 (t, 1H).

Provenance & Evidence