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

2,2,2-Trichloro-1-(1H-pyrrol-2-yl)-ethanone 57b (32 g, 151.8 mmol) was dissolved in 250 mL of dichloromethane followed by dropwise addition of a solution of iodine monochloride (25 g, 153 mmol) in 125 mL of dichloromethane. Upon completion of the addition, the reaction mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was washed with saturated aqueous sodium carbonate, aqueous sodium thiosulfate (2 M) and saturated brine successively, dried over anhydrous magnesium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)-ethanone 57c (47 g, yield 92%) as a yellow solid.

1. additionUpon completion of the addition
2. washThe mixture was washed with saturated aqueous sodium carbonate, aqueous sodium thiosulfate (2 M) and saturated brine successively
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. customto remove the drying agent
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-4294c4f831524387a01874cba807fb65

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367710B2