Novel high-yield iodination method using I2/NaNO3

[Rhodium]

A Novel Iodination of Aromatic Rings Using Iodine/Metallic Nitrate
M.S. Yusubov, et. al.

Bull. Korean Chem. Soc. 19(4), 400-401 (1998)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/aromatic.iodination.i2-nitrate.html)

Methoxybenzenes are selectively iodinated in high yield using I₂/NaNO₃/HOAc. This could be a new, easy way to 2C-I and DOI.

To a solution of 3 mmol methoxybenzene and 1.7mmol I2 in 10ml HOAc 0.3 mmol NaNO₃ was added at room temp, and the mixture heated at 85°C for 6h. Further additions of NaNO₃ (3x0.3mmol) was made after 1, 2 and 3h. Workup as usual after reducing residual I2 with 10% NaHSO₃.