Potassium Iodide → 3-Chloro-2-iodobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of sodium nitrite (4.82 g, 69.9 mmol) in water (25 mL) was added dropwise via addition funnel to a solution of 2-amino-3-chlorobenzoic acid (8.0 g, 46.6 mmol) in DMSO (25 mL) and 30% H2SO4 (75 mL) that had previously been cooled to 0° C. The mixture was stirred at 0° C. for 1 hour, at which time a solution of potassium iodide (19.3 g, 117 mmol) in water (25 mL) was added via addition funnel. The ice bath was removed, and the mixture was stirred for 2 hours. EtOAc (200 mL) was added, and the mixture was washed with 2N sodium sulfite (3×). The organic layer was then washed once with water and once with brine, dried over anhydrous MgSO4, and concentrated in vacuo to give 8.83 g of 3-chloro-2-iodobenzoic acid as a yellow solid.

Provenance & Evidence