1. 3-Trifluoromethoxyaniline (17.7 g, 100.00 mmol) was dissolved in H2O (80 ml) at -5 °C and an aqueous solution of NaNO2 (7.4 g, 115.62 mmol) was added.
2. H2SO4 (25 g, 250.00 mmol) was added slowly and dropwise with stirring, keeping the reaction temperature at -5 °C.
3. The reaction mixture was maintained at -5 °C for 15 min.
4. H2O (60 ml) solution of KI (20 g, 120.48 mmol) was added dropwise.
5. The reaction solution was brought to room temperature and stirred overnight.
6. The reaction mixture was extracted with EtOAc (2 x 100 mL).
7. The organic layers were combined, washed with Na2SO3/H2O (2 x 50 mL), dried over Na2SO4 and concentrated in vacuum.
8. The residue was purified by silica gel column chromatography to afford 1-iodo-3-(trifluoromethoxy)benzene (4.0 g, 14% yield).
