Methanol → Methyl 5-bromo-2-chlorobenzoate

Participants

Reaction Conditions

Reaction Steps

5-bromo-2-chlorobenzoic acid (E-Merck 8.14989.0101, 20 g; 84.94 mmol; 1 eq.) was dissolved in MeOH (400 mL). The solution was cooled down to 0° C. SOCl2 (18.49 mL; 254.82 mmol; 3 eq.) was added dropwise (addition took 30 min and IT increased to 9° C.). After addition, the reaction mixture was stirred at RT for 2 days. The reaction mixture was concentrated and the crude mixture was dissolved in EtOAc (400 mL) and washed with a saturated aqueous solution of NaHCO3 (100 mL), brine (100 mL), dried over MgSO4 and concentrated affording the title compound as a white solid (20.15 g, 95%). 1H NMR (DMSO-d6, 300 MHz) δ 7.98-7.97 (d, J=2.40 Hz, 1H), 7.80-7.67 (dd, J=8.74 Hz, 2.40 Hz, 1H), 7.56-7.54 (d, J=8.23 Hz, 1H), 3.86 (s, 3H). HPLC (Method A) Rt 4.15 min (Purity: 99.9%).

Provenance & Evidence