Iodine → 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-one

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Reaction Steps

Under a nitrogen atmosphere to a cold (0° C.) suspension of 2,2,2-Trichloro-1(1H-pyrrol-2-yl)ethanone (21.1 g, 99.3 mmol) and silver trifluoroacetate (23.2 g, 105 mmol) in chloroform was added iodine (25.4 g, 100 mmol) portionwise over 10 minutes. The mixture was allowed to warm to room temperature and stirred for 2 hours. This was filtered through celite and washed with chloroform. The organic phase was washed sequentially with 5% Na2S2O5, water, brine, dried (MgSO4) and filtered. Evaporation and trituration with 80% hexane/ether (80 mL) gave the title compound as a white solid (25.5 g, 78% yield), mp 140° C., 1H NMR (400 MHZ, CDCl3) δ 7.2 (m, 2H), 7.4 (m, 1H), (9.5 (bs, 1H), MS m/e (M+H)+ 339.

Provenance & Evidence