Potassium Iodide → 2-Chloro-1-iodo-4-methoxybenzene

Participants

Reaction Steps

Part H. A solution of the aniline from Part G (7.98 g, 50 mmol) in conc. HCl (25 mL) was cooled to −5° C., and treated dropwise with a concentrated aqueous solution of sodium nitrite (3.80 g, 55.1 mmol). After 30 minutes, the mixture was charged with 15 mL cyclohexane and 15 mL dichloromethane, then treated dropwise with a concentrated aqueous solution of potassium iodide (16.6 g, 100 mmol). This mixture was allowed to stir for 4 hours, then was extracted with dichloromethane (2×100 mL). The extracts were washed in sequence with 1 N aqueous sodium bisulfite (100 mL) and brine (60 mL), then combined, dried over magnesium sulfate, filtered and evaporated to afford sufficiently pure product, 3-chloro-4-iodoanisole (7.00 g, 26.1 mmol, 52%). TLC RF 0.39 (5:95 ethyl acetate-hexane). 1H NMR (300 MHz, CDCl3): d 7.69 (1H, d, J=8.8 Hz), 7.03 (1H, d, J=3.0 Hz), 6.57 (1H, dd, J=8.8, 3.0 Hz), 3.78 (3H, s). MS (H2O-GC/MS): m/e 269 (100).

Provenance & Evidence