2-Methylbenzoic acid → 5-Bromo-2-methylbenzoic acid

Participants

Reaction Steps

2-Methylbenzoic acid (40.0 g, 290 mmol) was added to a suspension of Br2 (160 mL) and iron powder (3.20 g, 57.0 mol) under N2 atmosphere in an ice bath. The mixture was allowed to warm to room temperature and was stirred for 2 hours. The reaction mixture was poured into water and the reddish solid was collected by filtration. The solid was dried under vacuum at 50° C. The solid was dissolved in 400 mL of methanol before 640 mL of 0.1N aqueous HCl was added at room temperature. The mixture was stirred and a white solid was produced. This solid was recrystallized from ethanol to afford 5-bromo-2-methyl-benzoic acid (12.0 g, 19%). 1H NMR (300M Hz, CDCl3) δ 8.17 (d, J=2.1, 1H), 7.56 (dd, J=8.1, 2.1, 1H), 7.15 (d, J=8.1, 1H), 2.59 (s, 3H).

Provenance & Evidence