BENZOIC ACID, 2-AMINO-4-CHLORO-5-IODO-, METHYL ESTER

Methyl 2-amino-4-chloro-5-iodobenzoate; To a mixture of iodine (68 g, 0.27 mol) and silver sulfate (84 g, 0.27 mol) in absolute EtOH (2.5 L) was added methyl 2-amino-4-chlorobenzoate (50 g, 0.27 mol). The reaction mixture was allowed to stir at rt for 45 min. The reaction mixture was then filtered through a pad of Celite.(R). and the filtrate was concentrated. The residue was dissolved in EtOAc (2 L) and washed with saturated aqueous NaHCOMethyl 2-amino-4-chloro-5-iodobenzoate To a mixture of IIntermediate 2 : Methyl 2-amino-4-chloro-5-iodobenzoateTo a solution of methyl 2-amino-4-chlorobenzoate (Aldrich, 1 11 g, 600 mmol) and silver sulfate (187 g, 600 mmol) in ethanol (1000 mL) was added dropwise in 8 hours a solution of iodine (152 g, 600 mmol) in ethanol (2000 mL). The reaction mixture was stirred overnight then filtered through a celite plug. The filtrate was concentrated under reduced pressure and the residue was triturated in n-heptane. The resulting solid was filtered, washed with diisopropyl ether to give the title compound methyl 2-amino-4-chloro-5-iodobenzoate (103.76 g, 334 mmol, 55.6percent yield) as a white powder. LCMS: (M+H)

Molecular Weight:311.50
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:310.92100
Monoisotopic Mass:310.92100
Topological Polar Surface Area:52.3
Heavy Atom Count:13
Complexity:203
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes