Thionyl Chloride → Methyl 4-bromo-2-chloro-5-fluorobenzoate

Participants

Reaction Steps

To a solution of 4-bromo-2-chloro-5-fluorobenzoic acid (25.40 g, 100.00 mmol) in methanol (300 mL) was added thionyl chloride (0.8 mL, 11.00 mmol) over 5 min at 0° C. The reaction mixture was heated to reflux for 8 h and then neutralized by slow addition of sodium bicarbonate (5.0 g) at 0° C. The solid was filtered out and washed with ethyl acetate (50 mL), the combined filtrate was concentrated in vacuo to afford the title compound as a pale yellow solid (24.7 g, 92%): 1H NMR (300 MHz, CDCl3) δ 7.68-7.60 (m, 2H), 3.91 (s, 3H).

Provenance & Evidence