Iodine → Methyl 4-amino-3-iodobenzoate
Reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.[I:12]I>C(O)C.S([O-])([O-])(=O)=O.[Ag+2]>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:10][C:11]=1[I:12]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
Methyl 4-aminobenzoate (30.23 g, 200 mmol) was added to a mixture of iodine (60.91 g, 240 mmol) and silver sulfate (81.07 g, 260 mmol) in 1 L of ethanol at room temperature. The mixture was stirred at room temperature for 18 hours, filtered over Celite and the filtrate was evaporated to dryness under reduced pressure. The residue was chromatographed on silica gel (230–400 mesh) and eluted with 1% ethyl acetate in hexane to give 35 g (63%).
Workup
- filtrationfiltered over Celite
- customthe filtrate was evaporated to dryness under reduced pressure
- customThe residue was chromatographed on silica gel (230–400 mesh)
- washeluted with 1% ethyl acetate in hexane
- customto give 35 g (63%)
Sources & evidence
- ORD record
- ord-f7ee27120d3e45df9a00b6188ab0a4c8
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07098231B2
Reaction notes
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