Methyl 2-amino-5-iodo-4-trifluoromethylbenzoate.

https://www.google.com/patents/WO2006002342A1?cl=en

 Preparation of methyl 2-amino-5-iodo-4-trifluoromethylbenzoate.

Add a solution of methyl 2-amino-4-trifluoromethylbenzoate (178 g, 812 mmol) in ethanol (3.3 L) to a suspension of iodine (206.1 g, 812 mmol) and silver(II) sulfate (253 g, 812 mmol) in ethanol (5 L) at room temperature under an atmosphere of nitrogen and stir for 2 h. Filter the suspension through a pad of a Celite®, wash the pad with additional ethanol (2 L) and remove the solvents from the combined filtrates under reduced pressure at 40 °C. Dissolve the residue in ethyl acetate (7.5 L) and wash with saturated sodium bicarbonate solution (3 X 1.5 L), water (3 X 1.5 L) and brine (2 L). Dry the organic phase over anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure to give the title compound as a pale brown crystalline solid (276.0 g, 99%). ¹H NMR (300 MHz, CDCl₃) D 
8.39 (1 H, s), 
6.99 (1 H, s), 
5.93 (2 H, s), NH2
3.90 (3 H, s).