Hydrochloric Acid → Methyl 4-cyano-2-fluorobenzoate

Participants

Reaction Steps

4-Cyano-2-fluorobenzoic acid (ABCR, 16 g; 96.90 mmol) was suspended in 300 mL of DCM. Oxalyl chloride (9 mL; 106.59 mmol) was added, followed by DMF (0.5 mL). After 3 hours at RT the yellow solution was evaporated under reduced pressure and the resulting yellow oil was taken up in anhydrous THF (150 mL) and added dropwise to a 4° C. solution of methanol (50 mL) and triethylamine (25.80 mL; 193.79 mmol; 2 eq.). An HCl solution (0.1 N, 200 mL) was added and the product was extracted with EtOAc (3×100 mL). The combined organic phases were washed with a semi-saturated NaHCO3 solution (200 mL), water (200 mL) and dried over MgSO4. Evaporation under reduced pressure gave the title compound as a light yellow solid (17.84 g, quantitative). HPLC (Method A) Rt 2.81 min (Purity: 93.9%).

Provenance & Evidence