Nitrogen → 1-Iodo-3,5-dimethoxybenzene

Participants

Reaction Conditions

Reaction Steps

To an ice-salt cooled solution of 4.55 g (29.7 mmol) of 3,5-dimethoxyaniline in 50 mL of water was added 4 mL of 98% H2SO4. After the solution had cooled to −5° C., a solution of 2.4 g (34.8 mmol) of NaNO2 in a minimum amount of water was added, keeping the temperature below 0° C. The reaction was stirred for 10 min, then 50 mL of diethyl ether was added. A solution of 15 g (90 mmol) of potassium iodide in a minimum amount of water was added slowly to control the evolution of N2. After 3 h, the layers were separated, and the aqueous layer was extracted with additional ether (2×50 mL). The combined ether layers were back extracted with 5% (w/v) NaHSO3(aq) (2×50 mL), 1 M HCl (1×50 mL), 2M NaOH (1×50 mL), then brine (1×25 mL), dried over MgSO4, filtered, and concentrated to a dark oil. The product was purified by silica gel chromatography, eluting with 10% ethyl acetate:hexanes to provide the titled compound (4.80 g, 61%).

Provenance & Evidence