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

Participants

Reaction Conditions

Reaction Steps

Iodine (1.2 g, 4.7 mmol) was added portion wise to a solution of 2,2,2-trichloro-1-(1H-pyrrol-2-yl)ethanone (1 g, 4.7 mmol) and silver trifluoroacetate (1.1 g, 5 mmol) in dry dichloromethane (24 mL), cooled to 0° C. The reaction mixture was allowed to warm up slowly to 18° C. (water bath) and stirred at the same temperature for 5 h. The solid was filtered, the organic phase washed with Na2S2O5 (5% aq. solution) until decoloration occurs and finally washed with H2O (1×20 mL). The organic phase was dried over Na2SO4 and filtered through a plough of SiO2 (hexane-EtOAc 4:1), to obtain compound 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethanone (IX) as an off-white solid (1.49 g, 94% yield).

Provenance & Evidence