Methanol → Methyl 4-Bromo-2-chlorobenzoate

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-chlorobenzoic acid (COMBI-BLOCK; CA-4187; 1 000 mg; 4.25 mmol; 1 eq.) was dissolved in MeOH (20 mL). The resulting solution was cooled down to 0° C. and thionyl chloride (1.23 mL; 16.99 mmol; 4 eq.) was added dropwise. After addition, the reaction mixture was stirred at RT. As the reaction was complete, solvents were evaporated. The crude mixture was dissolved in EtOAc and washed with NaHCO3 sat. and NaCl sat. solutions. The organic phase was dried over MgSO4, filtrated and evaporated to give the title compound (871 mg, 82%). 1H NMR (CDCl3, 300 MHz) δ 7.72 (d, J=8.3 Hz, 1H), 7.64 (d, J=1.9 Hz, 1H), 7.46 (dd, J=8.5, 1.9 Hz, 1H), 3.93 (s, 3H). HPLC (Method A) Rt 4.22 min (Purity: 98.5%).

Provenance & Evidence