Sulfuric Acid → 5-Iodo-2-methyl anisole

Participants

Reaction Steps

5-amino-2-methylanisole (8.05 g, 58.7 mmol) was dissolved in 244 mL water and 8.1 mL concentrated H2SO4 and cooled to 0° C. NaNO2 (4.86 g, 70.4 mmol) in 61 mL water was added dropwise with stirring. Reaction was stirred 30 minutes at 0° C. Urea (0.70 g, 11.7 mmol) was added and stirring continued for an additional 30 minutes. The pale yellow solution was transferred to a dropping funnel and added slowly to a stirred solution of potassium iodide (19.48 g, 117.4 mmol) in 122 mL water. The solution was stirred at ambient temperature for 1 h after completion of the addition. The reaction was extracted with diethyl ether (3×300 mL). The organic extracts were combined and washed with 1M Na2S2O3 (2×200 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 9.60 g (66%) of 5-iodo-2-methyl anisole as a brown oil.

Provenance & Evidence