Hydrochloric Acid → 5-Chloro-2-(4-fluorophenoxy)benzoic acid

Participants

Reaction Steps

A mixture of methyl 5-chloro-2-(4-fluorophenoxy)benzoate (step 1, 2.60 g, 9.26 mmol), tetrahydrofuran (20 mL), methanol (20 mL), and 2 N sodium hydroxide (20 mL) was stirred at room temperature for 3 h. The mixture was poured into 2 N hydrochloric acid (50 mL) and the aqueous mixture was extracted with ethyl acetate (200 mL). The organic layer was dried over magnesium sulfate and evaporated to give 2.41 g (98%) of the title compound as white solids: 1H-NMR (CDCl3) δ 8.11 (1H, d, J=2.8 Hz), 7.43 (1H, dd, J=9.0, 2.8 Hz), 7.14–7.02 (4H, m), 6.80 (1H, d, J=8.8 Hz); MS (ESI) m/z 265 (M−H)−.

Provenance & Evidence