Hydrochloric Acid → 4-Azidotetrafluorobenzoic acid

Participants

Reaction Steps

A solution of 1.009 g (4.0 mmol) of methyl 4-azido-2,3,5,6-tetrafluorobenzoate in 4 mL (10 mmol) of 10% NaOH, and 20 mL of methanol was stirred at room temperature for 12 hours. This solution was carefully acidified in an ice bath with approximately 10 mL of 1.2 M HCl to a pH<2. The acidified solution was extracted with chloroform (3×10 mL), dried over anhydrous sodium sulfate, and evaporated to afford 4-azidotetrafluorobenzoic acid (0.9181 g, 96%) as white flakes, mp 141.6-142.8° C.

Provenance & Evidence