Sulfuric Acid → 2-Bromo-4-iodo-1-methylbenzene

Participants

Reaction Conditions

Reaction Steps

To a vigorously stirred mixture of 3-bromo-4-methylaniline (40 g, 215 mmol), sulfuric acid (360 mL) and H2O (900 mL) at 0° C. was added dropwise a NaNO2 solution (16.6 g, 240 mmol in 80 mL of H2O). The mixture was stirred at 0° C. for 1 hour and a solution of potassium iodide (64 g, 387 mmol in 160 mL of H2O) was added. The reaction was stirred for 8 hours at r.t. The aqueous layer was extracted with Et2O and the combined organic layers were washed with a 10% aqueous solution of Na2S2O3, dried over Na2SO4 and concentrated. The residue was filtered through a silica gel pad eluted with 10% EtOAc/hexane and concentrated to give 60 g of the title compound as a reddish syrup used as such.

Provenance & Evidence