Hydrochloric Acid → HCID 118005931, compound

Participants

Reaction Conditions

Reaction Steps

8 (3.4 g, 9.9 mmol) was suspended in concentrated HCl (17 mL) at 0° C. and stirred for 30 min. After this period, a solution of NaNO2 in H2O (0.6 g in 9.2 mL, 19 mmol) was added dropwise. Then the resulting mixture was stirred for 1 h at room temperature. This solution was added over 30 min to a solution of CuCl (16.6 g, 40 mmol) in concentrated HCl (17.0 mL) at 65° C. After addition, the mixture was heated at 80° C. for 30 minutes. The mixture was allowed to cool to room temperature before addition of brine. The solution was extracted with ethyl acetate, dried over anhydrous MgSO4, evaporated by rotary evaporation, and purified by column chromatography to give 1-chloro-3-iodo-5-(2-methoxyphenoxy)benzene (9) (1.5 g, 42%). 1H NMR (400 MHz, CDCl3) δ 7.35 (t, J=1.6 Hz, 1H), 7.23-7.15 (m, 1H), 7.13 (dd, J=2.2, 1.4 Hz, 1H), 7.06-6.94 (m, 3H), 6.83 (t, J=2.0 Hz, 1H), 3.82 (d, J=4.5 Hz, 3H).

Provenance & Evidence