Nitric Acid → 3-bromo-4-tert-butylbenzoic acid

Participants

Reaction Steps

4-tert-butyl benzoic acid (500 mg, 2.8 mmol) was stirred rapidly in acetic acid (11 mL), nitric acid (1.7 mL) and bromine (114 μL, 5.9 mmol). To this was added a solution of silver nitrate (1.01 g, 5.9 mmol) in water (5 mL). A thick yellow precipitate resulted and further acetic acid was added (2 mL) before heating at reflux for 1 h. The hot solution was filtered and water added to the filtrate until a white solid precipitated. The solid was filtered, air dried and recrystallised from acetic acid to give 3-bromo-4-tert-butyl-benzoic acid as a white solid (263 mg, 36%). 1H NMR (CDCl3, 300 MHz) δ 1.85 (s, 9H, (CH3)3), 7.86 (d, 1H, J=8.5 Hz, ArH), 8.26 (dd, 1H, J=2.0, 8.5 Hz, ArH), 8.62 (d, 1H, J=2.0 Hz).

Provenance & Evidence