Iodine → Methyl 2-amino-4-chloro-5-iodobenzoate

HRID 1858083Notes

Reaction equation

HRID 1858083 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[NH:11]C(=O)C.[I:16]I>FC(F)(F)S([O-])(=O)=O.[Ag+]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([I:16])[C:7]([Cl:10])=[CH:6][C:5]=1[NH2:11]

Participants

4

Reactant 2

HCID 807IodineHCID 2800203Benzoic acid, 2-(acetylamino)-4-chloro-, methyl ester

Product 1

HCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoateYield 82.6%

Reagents, catalysts & solvents 1

HCID 76223Silver(I) trifluoromethanesulfonateCatalyst

Procedure

To a suspension of 2-acetylamino-4-chlorobenzoic acid methyl ester (2.0 g in 80 mL of dry chloroform) and 2.5 g silver trifluoromethanesulfonate was added iodine (2.87 g in 40 mL chloroform) and the mixture stirred at room temperature. After 5 hours, the mixture was filtered over diatomaceous earth and the filtrate concentrated in vacuo. Purification of the resulting oil by flash chromatography on silica gel (hexane:ethyl acetate, 95:5; then 90:10) gave the title compound (2.26 g).

Workup

  1. filtrationthe mixture was filtered over diatomaceous earth
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification of the resulting oil by flash chromatography on silica gel (hexane

Sources & evidence

ORD record
ord-24acdfef56a14e40b320a0f8063888a5
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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