Trifluoromethanesulfonic anhydride → 1-Chloro-2-iodo-5-methoxy-4-nitrobenzene

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Reaction Steps

To a solution of H2SO4 (600 mL, 90%), trifluoromethanesulfonic anhydride (11.3 g, 0.04 mol) and NIS (49.68 g, 0.22 mol) were added and resulting mixture was stirred at room temperature for 1 h. To this mixture, 4-chloro-2-methoxy-1-nitrobenzene (69 g, 0.368 mol) was added quickly. The mixture was stirred for 1 h, and then NIS (33.12 g, 0.148 mol) was slowly added to the mixture. The mixture was stirred at room temperature for 1 h and then was poured into ice-water. The precipitate collected by filtration, rinsed with water, aqueous NaSO3 and NaHCO3 solutions, and then dried in vacuo to afford the desired product (113 g, 98% yield).

Provenance & Evidence