Hydrochloric Acid → 6-Chloro-3-fluoro-2-methylbenzoic acid

Participants

Reaction Steps

Methyl 6-chloro-3-fluoro-2-methylbenzoate 65 (14 g, 69 mmol, 1 eq) and NaOH (13.8 g, 345 mmol, 5 eq) were dissolved in a mixture of 1,4-dioxane (10 mL) and H2O (130 mL), and the resulting mixture was stirred at reflux overnight. The reaction mixture was cooled to RT and neutralized with conc. HCl to adjust the pH value to 1. The mixture was extracted with DCM (3×60 mL). The combined organic layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo to afford the product 6-chloro-3-fluoro-2-methylbenzoic acid 66. The product was used directly in the next step.

Provenance & Evidence