Hydrogen Bromide → 5-(3-bromophenyl)pentanoic Acid

Participants

Reaction Steps

To a solution of 5-(3-Bromo-phenyl)-pent-4-enoic acid (4 g, 16 mmol) in EtOAc (150 mL) was added Pd/C (400 mg) and a solution of 40% HBr in AcOH (0.5 mL). The mixture was stirred at rt under 1 atm of hydrogen for 1 h. The reaction mixture was filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography using a solvent system of 5:1 petroleum ether/EtOAc to give 5-(3-Bromo-phenyl)-pentanoic acid (3.2 g, 80%). 1H-NMR (400 MHz, CDCl3) δ ppm 7.3-7.4 (m, 2H), 7.05-7.15 (m, 2H), 2.55 (s, 2H), 2.35 (s, 2H), 1.7 (m, 4H).

Provenance & Evidence