Rhodium
(Chief Bee)
01-27-01 01:07
No 169606
      Novel high-yield iodination method using I2/NaNO3
(Rated as: excellent)
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A Novel Iodination of Aromatic Rings Using Iodine/Metallic Nitrate
M.S. Yusubov, et. al.
Bull. Korean Chem. Soc. 19(4), 400-401 (1998) (../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 85C 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.