Chemical Properties
colorless to light yellow liquid
Uses
3-Amino-4-iodobenzotrifluoride is a useful intermediate for the preparation of trifluoromethylindoles by coupling-annulation of alkynes with iodo(trifluoromethyl)anilines.
Synthesis
General procedure for the synthesis of 2-iodo-5-trifluoromethylaniline from 3-nitro-4-iodobenzotrifluoride: Iron powder (750 mg, 13.43 mmol) was added to a mixed HOAc-EtOH solution (10 mL, 1:5, v/v) of 3-nitro-4-iodobenzotrifluoride (850 mg, 2.68 mmol) at 23 °C. The reaction mixture was stirred at 23 °C for 3 h. The reaction was subsequently quenched with saturated NaHCO3 solution (20 mL) and diluted with EtOAc (50 mL). The organic and aqueous layers were separated and the organic layer was washed with deionized water (3 x 10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by fast column chromatography (silica gel as stationary phase, eluent hexane:EtOAc, 10:1, v/v) to afford 2-iodo-5-trifluoromethylaniline (754 mg, 98% yield) as a yellow solid.1H NMR (400 MHz, CDCl3) δ = 7.76 (dd, J = 8.2,0.7Hz, 1H), 6.96 (d, J = 1.7 Hz, 1H), 6.72 (ddd, J=8.2,2.0,0.6 Hz, 1H), 4.32 (brs, 2H). Mass spectrum (ESI) m/z: 288.0 [M+H]+.
References
[1] Patent: WO2016/29310, 2016, A1. Location in patent: Paragraph 00357-00359
[2] Patent: US5079245, 1992, A
[3] Angewandte Chemie - International Edition, 2011, vol. 50, # 32, p. 7354 - 7358
[4] Patent: US5998334, 1999, A
[5] Organic Letters, 2017, vol. 19, # 17, p. 4484 - 4487
