反应详情

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 (3×1.5 L), water (3×1.5 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) δ 8.39 (1H, s), 6.99 (1H, s), 5.93 (2H, s), 3.90 (3 H, s).

1. filtrationFilter the suspension through a pad of a Celite®
2. washwash the pad with additional ethanol (2 L)
3. customremove the solvents from the combined filtrates under reduced pressure at 40° C
4. dissolutionDissolve the residue in ethyl acetate (7.5 L)
5. washwash with saturated sodium bicarbonate solution (3×1.5 L), water (3×1.5 L) and brine (2 L)
6. dry with materialDry the organic phase over anhydrous magnesium sulfate
7. filtrationfilter
8. customremove the solvent under reduced pressure