2-IODO-4-TRIFLUOROMETHOXYANILINE synthesis

Yield:845866-79-7 78%

Reaction Conditions:

with bis(pyridine)iodonium(I) tetrafluoroborate in dichloromethane; for 0.333333 h;

Steps:

2.2.1. 4-(Trifluoromethoxy)-2-iodoaniline (2e)

4-(Trifluoromethoxy)aniline (1.47 g, 8.25 mmol) was dissolved in dichloromethane(20 mL), and IPy2BF4 was added (3.07 g, 8.25 mmol) in one portionwith stirring. The reaction was stirred for 20 min, after which water (20 mL) was added. The mixture was extracted with CH2Cl2 (2 × 10 mL), washed withaq. Na2S2O4, and the organic layer was dried over Na2SO4. Following filtrationand concentration in vacuo, the resulting residue was purified by silica gelchromatography (2:1 hexanes:EtOAc) to give 2e as a dark brown oil (1.95 g,78.0%): 1H NMR (CDCl3, 360 MHz) δ 7.51 (d, 1H, J = 1.8 Hz, H3), 7.04 (dd,1H, J = 8.7, 2.8 Hz, H5), 6.71 (d, 1H, J = 8.7 Hz, H6), 3.89 (v br, 2H, NH2).

References:

Benitah, Avi;Qualley, Dominic F.;Woski, Stephen A. [Nucleosides, nucleotides and nucleic acids,2022,vol. 41,# 11,p. 1187 - 1204]