Sulfuric Acid → 5-Bromo-2-acetylsalicylic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2-hydroxy-5-bromo-benzoic acid (5.0 g, 23.0 mmol) in acetic anhydride (7.1 mL, 75.4 mmol) was added conc. H2SO4 (0.35 mL) at rt. Resulting suspension was heated in a 100° C. oil bath for 25 min. After cooled to about 50° C., the reaction mixture was poured onto ice (100 g) with stirring. The precipitated product was collected, rinsed with water, and dried in vacuo to give the title compound (5.56 g). 1H NMR (200 MHz, CDCl3): δ (ppm)=8.21 (d, J=2.3 Hz, 1H), 7.71 (dd, J=8.6, 2.3 Hz, 1H), 7.01 (d, J=8.6 Hz, 1H), 2.34 (s, 3H).

Provenance & Evidence