2-Chloro-4-hydroxybenzoic acid → 2-Chloro-4-hydroxy-5-iodobenzoic acid

Participants

Reaction Steps

2-Chloro-4-hydroxybenzoic acid (5.18 g, 30.02 mmol) was dissolved in trifluoromethanesulfonic acid (25 g) and N-iodosuccinimide (6.75 g, 30.00 mmol) was added by portions at 0° C. After stirring at room temperature for 15 hr, trifluoromethanesulfonic acid (25 g) was further added, and N-iodosuccinimide (2.02 g, 8.98 mmol) was added by portions at 0° C. After stirring at room temperature for 13.5 hr, the reaction mixture was added to ice water (300 ml), and the mixture was stirred for 2 hr. The precipitated solid was collected by filtration, washed with water, and vacuum dried to give a mixture (8:2) (5.76 g) of 2-chloro-4-hydroxy-5-iodobenzoic acid and 2-chloro-3,5-diiodo-4-hydroxybenzoic acid.

Provenance & Evidence