Iodine synthesis

12synthesis methods

Product Name:Iodine
CAS Number:7553-56-2
Molecular formula:I2
Molecular Weight:253.81

In the United States, the principal method used to recover iodine from oil brines involves the oxidation of iodide by chlorine, followed by removal of the volatile iodine from solution with an airstream. The iodine is reabsorbed in solution and reduced to hidrotic acid with sulfur dioxide. The solution is then chlorinated to precipitate free iodine, which is further purified by treatment with concentrated sulfuric acid. The same process is used to recover iodine from natural brines. In the recovery of iodine from Chilean nitrate deposits, solutions containing the iodates are reduced with sodium bisulfite to precipitate the iodine, which is then purified by sublimation.

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Yield:7553-56-2 66%

Reaction Conditions:

Stage #1: N-trifluoroacetic-3-nitroanilinewith sodium hydride in tetrahydrofuran at 0; for 1 h;
Stage #2: methyl iodide in tetrahydrofuran at 20;

Steps:

9

EXAMPLE 9 Synthesis of Compound 97 A solution of nitroaniline (1.0 g, 7.13 mmole) in CH2Cl2 (25 ML) was treated with pyridine (2.9 ML, 36 mmole) and trifluoroacetic anhydride (5 ML, 36 mmole) and stirred at ambient temperature for 3 hours.. The reaction was diluted further with CH2Cl2, washed with IN HCl and brine, dried (MgSO4) and concentrated in vacuo to yield I1 (1.61 g, 95%) as a white solid.. The 1H NMR was consistent with that of the desired structure. . To a slurry of NaH (60% oil dispersion; 34 mg, 1.42 mmole) in THF (10 ML) at 0° C. was added a solution of I1 (200 mg, 0.85 mmole) in THF (10 ML) and the mixture stirred for 1 hour.. To this was added methyl iodide (100 μL, 1.7 mmole) and the mixture was stirred overnight at ambient temperature.. The reaction was poured into water and extracted with EtOAc. The organics were separated, dried (MgSO4) and concentrated in vacuo.. Pure I2 was obtained through flash chromatography, eluding with 5% EtOAc in hexanes, in a yield of 163 mg (66%) as a yellow solid..

References:

US6344465,2002,B1 Location in patent:Page column 30