3-Methyl-2-nitrophenol → 4-Bromo-3-methyl-2-nitrophenol

Participants

Reaction Conditions

Reaction Steps

An ice cold suspension of 3-methyl-2-nitrophenol (6.26 g, 40.9 mmol) in acetic acid (20 mL) was treated with a solution of bromine (1.895 mL, 36.8 mmol) in acetic acid (5.0 mL) over 10 minutes using a syringe pump. The mixture was stirred for one hour at 0° C. The mixture was poured into ice water and then extracted with ethyl acetate. The extracts were washed with 5% sodium bicarbonate (2×50 mL), dried over MgSO4, filtered and then concentrated. The residue was purified on silica gel (hexanes/dichloromethane 0-70% gradient) to afford a bright yellow solid (6.66 g, 70%): 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 9.32 (s, 1 H), 7.67 (d, J=9.0 Hz, 1 H), 6.93 (d, J=9.0 Hz, 1 H), 2.64 (s, 3 H); LC/MS (m/z) ES+=230 (M−1).

Provenance & Evidence