Acetic Acid → 2-Iodo-4-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

Solid potassium iodide (55 g, 0.33 mol) was added in one portion to a suspension of 2-iodosyl-4-nitro-benzoic acid I-1a (54.9 g, 0.18 mol) in water (250 ml) and glacial acetic acid (50 ml). Over the next 5-10 minutes, the solids gradually went into solution and the solution turned from off-white to red. After stirring for one hour at 23° C., gaseous sulfur dioxide was bubbled through the reaction mixture until the red color dissipated and a pale green suspension had formed. The solids were collected by filtration, co-evaporated from toluene (3×250 ml), and dried in vacuo to affort 2-iodo-4-nitrobenzoic acid I-1b (33 g, 64%).

Provenance & Evidence