Sodium Bicarbonate → 4-(2-Bromoethoxy)-3-fluorobenzoic acid

Participants

Reaction Steps

4-(2-Bromoethoxy)-3-fluorobenzonitrile (3.78 g, 15.5 mmol) in water (18 mL) and concentrated sulfuric acid (18 mL) was heated at 110° C. for 12 hours. The solution was then cooled to room temperature and neutralized with solid sodium bicarbonate. Acidification with glacial acetic acid leads to a white solid precipitate, which was collected by filtration and dissolved in dichloromethane. The resulting solution was dried over anhydrous sodium sulfate, filtered, and concentrated to give the product as a beige-colored solid (2.65 g, 65% yield). 1H NMR (400 MHz, DMSO-d6) δ 13.00 (brs, 1H), 7.44 (d, J=8.4 Hz, 1H), 7.69 (d, J=12.0 Hz, 1H), 7.29 (dd, J=8.8 Hz, 8.4 Hz, 1H), 4.48 (t, J=5.2 Hz, 2H), 3.85 (t, J=5.2 Hz, 2H).

Provenance & Evidence