Ammonium Chloride → HCID 118005911, compound

Participants

Reaction Conditions

Reaction Steps

7 (4.9 g, 13 mmol), Fe (5.9 g, 100 mmol) and a solution of NH4Cl (2.3 g in 23 mL H2O, 42 mmol) were suspended in 67 mL of EtOH and heated at 75° C. for 6 h. The mixture was allowed to cool to room temperature, filtered over celite, and concentrated by rotary evaporation. The residue was partitioned between EtOAc and water; combined organic extracts were dried over anhydrous Na2SO4, concentrated by rotary evaporation, and purified by column chromatography to give 3-iodo-5-(2-methoxyphenoxy)aniline (8) (3.4 g, 77%). 1H NMR (600 MHz, CDCl3) δ 7.18-7.13 (m, 1H), 7.00 (ddd, J=7.7, 5.7, 1.5 Hz, 2H), 6.94 (td, J=7.7, 1.4 Hz, 1H), 6.83-6.79 (m, 1H), 6.71-6.68 (m, 1H), 6.30 (t, J=2.0 Hz, 1H), 3.82 (s, 3H).

Provenance & Evidence