Iodine → 2,2,2-trichloro-1-(4-iodo-1H-pyrrol-2-yl)ethan-1-one
Reaction equation
[I:1]I.[Cl:3][C:4]([Cl:13])([Cl:12])[C:5]([C:7]1[NH:8][CH:9]=[CH:10][CH:11]=1)=[O:6].O>ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[Cl:13][C:4]([Cl:3])([Cl:12])[C:5]([C:7]1[NH:8][CH:9]=[C:10]([I:1])[CH:11]=1)=[O:6]Participants
6
Conditions
- Temperature
- 0 °C
Procedure
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).
Workup
- filtrationThe solid was filtered
- washthe organic phase washed with Na2S2O5 (5% aq. solution) until decoloration
- washfinally washed with H2O (1×20 mL)
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered through a plough of SiO2 (hexane-EtOAc 4:1)
Sources & evidence
- ORD record
- ord-000619da75614e54a6c9d99898089d8a
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08981092B2
Reaction notes
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