Methanol → Methyl 2-chloro-4-cyano-5-methoxybenzoate

Participants

Reaction Conditions

Reaction Steps

2-chloro-4-cyano-5-methoxybenzoic acid (600 mg; 2.84 mmol; 1 eq.) was dissolved in MeOH (12 mL). The solution was cooled down to 0° C. SOCl2 (0.62 mL; 8.51 mmol; 3 eq.) was added dropwise. The reaction mixture was stirred at RT for 24 hours. The reaction mixture was concentrated and the residue was taken up in EtOAc. The organic layer was washed with a saturated aqueous solution of NaHCO3, then brine, dried over MgSO4, concentrated affording the title compound as a yellow solid (0.58 g, 90%). 1H NMR (DMSO-d6, 300 MHz) δ 8.09 (s, 1H), 7.57 (s, 1H), 3.96 (s, 3H), 3.89 (s, 3H). HPLC (Method A) Rt 4.08 min (Purity: 94.3%).

Provenance & Evidence