Hydrochloric Acid → 4-Azidotetrafluorobenzoic acid

Reaktionsgleichung

[N:1]([C:4]1[C:13]([F:14])=[C:12]([F:15])[C:7]([C:8]([O:10]C)=[O:9])=[C:6]([F:16])[C:5]=1[F:17])=[N+:2]=[N-:3].[OH-].[Na+].Cl>CO>[N:1]([C:4]1[C:5]([F:17])=[C:6]([F:16])[C:7]([C:8]([OH:10])=[O:9])=[C:12]([F:15])[C:13]=1[F:14])=[N+:2]=[N-:3]

Komponenten

Versuchsvorschrift

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.