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Iodobenzene reacts readily with magnesium to form the Grignard reagent, phenylmagnesium iodide. Phenylmagnesium iodide, like the bromide analog, is a synthetic equivalent for the phenyl anion synthon. Iodobenzene reacts with chlorine to give the complex, iodobenzene dichloride, [4] which is used as a solid source of chlorine.
The compound can be prepared by reaction of iodobenzene with a mixture of trifluoroperacetic acid and trifluoroacetic acid in a method analogous to the synthesis of (diacetoxyiodo)benzene: [1] It can also be prepared by dissolving diacetoxyiodobenzene (a commercially-available compound) with heating in trifluoroacetic acid: [ 2 ]
This reagent was originally prepared by Conrad Willgerodt [3] by reacting iodobenzene with a mixture of acetic acid and peracetic acid: [4] [5] C 6 H 5 I + CH 3 CO 3 H + CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 + H 2 O. PIDA can also be prepared from iodosobenzene and glacial acetic acid: [5] C 6 H 5 IO + 2 CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 ...
The iodobenzene diacetate product hydrolyzes to the polymeric iodosobenzene (PhIO), which is stable in cool alkaline solution. [6] In hot water (or, in Willgerodt's original preparation, steam distillation), iodosobenzene instead disproportionates to iodoxybenzene and iodobenzene: [7] 2 PhIO → PhIO 2 + PhI
Preparation [ edit ] In one laboratory route to 1-bromo-4-iodobenzene, 4-bromoaniline is treated with concentrated sulfuric acid and sodium nitrite to form the diazonium salt, which is then treated with potassium iodide to form 1-bromo-4-iodobenzene.
Iodobenzenes are a group of aryl iodides/halobenzenes consisting of one or more iodine atoms as substituents on a benzene core. They have the formula C 6 H 6–n I n, where n = 1–6 is the number of iodine atoms.
Iodobenzene dichloride is not stable and is not commonly available commercially. It is prepared by passing chlorine gas through a solution of iodobenzene in chloroform, from which it precipitates. [3] The same reaction has been reported at pilot plant scale (20 kg) as well. [4] Ph-I + Cl 2 → PhICl 2
Iodosobenzene is prepared from iodobenzene. [3] It is prepared by first oxidizing iodobenzene by peracetic acid. Hydrolysis of resulting diacetate affords "PhIO": [4] C 6 H 5 I + CH 3 CO 3 H + CH 3 CO 2 H → C 6 H 5 I(O 2 CCH 3) 2 + H 2 O C 6 H 5 I(O 2 CCH 3) 2 + H 2 O → C 6 H 5 IO + 2 CH 3 CO 2 H. The structure of iodosobenzene has been ...