Iodine → Methyl 2-amino-4-chloro-5-iodobenzoate
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)C([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
Product 1
Reagents, catalysts & solvents 1
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 trifluoroacetate 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
- filtrationthe mixture was filtered over diatomaceous earth
- concentrationthe filtrate concentrated in vacuo
- customPurification of the resulting oil by flash chromatography on silica gel (hexane
Sources & evidence
- ORD record
- ord-034b90ab6aed494aa691454dfa215d2f
- Source dataset
- uspto-grants-2000_11
- Patent number
- US06147088
Reaction notes
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