Hydrochloric Acid → 2-Azido-4-bromobenzoic acid

Participants

Reaction Steps

To a solution of 2-amino-4-bromobenzoic acid (8.4 g, 0.039 mol) in a mixture of concentrated HCl (70 mL) and H2O (100 mL) was added a solution of NaNO2 (2.8 g, 0.044 mol) in H2O (40 mL) such that the reaction temperature did not rise above 5° C. After addition was complete the resulting slurry was stirred for 15 min and the cold mixture added in aliquots to a solution of NaN3 (2.5 g, 0.039 mol) and NaOAc (38 g, 0.47 mol) in H2O (80 mL) at room temperature. The resulting slurry was stirred for 30 min and the solid collected by filtration giving 6.4 g (68% yield) of product as a tan powder. 1H NMR (360 MHz, DMSO): 7.46 (1H, dd, J 1.4 and 7.5 Hz), 7.57 (1H, d, J 1.4 Hz), 7.70 (1H, d, J 7.5 Hz).

Provenance & Evidence