Iodine → Methyl 4-amino-3-iodobenzoate

HRID 2252736Notes

Reaction equation

HRID 2252736 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

HCID 807IodineHCID 12082Methyl 4-aminobenzoate

Product 1

HCID 4104649Methyl 4-amino-3-iodobenzoate

Reagents, catalysts & solvents 2

HCID 178418844HCID 178418844, compoundCatalystHCID 702EthanolSolvent

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

  1. filtrationfiltered over Celite
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customThe residue was chromatographed on silica gel (230-400 mesh)
  4. washeluted with 1% ethyl acetate in hexane
  5. customto give 35 g (63%)

Sources & evidence

ORD record
ord-80cadde378c34bda85584da1bb4877b9
Source dataset
uspto-grants-2008_01
Patent number
US07323470B2

Reaction notes

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