methyl 2-amino-5-iodo-4-(trifluoromethyl)benzoate

Step 3; Preparation of methyl 2-amino-5-iodo-4-trifluoromethylbenzoate; Add a solution of methyl 2-amino-4-trifluoromethylbenzoate (178 g, 812 mmol) inethanol (3.3 L) to a suspension of iodine (206.1 g, 812 mmol) and silver(II) sulfate (253g, 812 mmol) in ethanol (5 L) at room temperature under an atmosphere of nitrogen andstir for 2 h. Filter the suspension through a pad of a Celite.(R)., wash the pad withadditional ethanol (2 L) and remove the solvents from the combined filtrates underreduced pressure at 40 °C. Dissolve the residue in ethyl acetate (7.5 L) and wash withsaturated sodium bicarbonate solution (3 x 1.5 L), water (3 x 1.5 L) and brine (2 L). Drythe organic phase over anhydrous magnesium sulfate, filter and remove the solvent underreduced pressure to give the title compound as a pale brown crystalline solid (276.0 g, 99percent).2-Amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester; A mixture of 2-amino-4-trifluoromethyl-benzoic acid methyl ester (51.5 g, 235 mmol), iodine (55.1 g, 217 mmol) and silver sulfate (73.3 g, 234 mmol) in EtOH (1560 mL) was stirred for 1 h at r.t. under nitrogen. The suspension was then filtered and the filtrate diluted with EtOAc and washed once with a 10percent aqueous sodium thiosulfate solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give 2-amino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (67.5 g, 196 mmol, 83percent) as a brown solid, m.p. 101-103

Molecular Weight:345.06
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:2
Exact Mass:344.94736
Monoisotopic Mass:344.94736
Topological Polar Surface Area:52.3
Heavy Atom Count:16
Complexity:272
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes