Suzuki, Hitomi published the artcileJacobsen reaction. V. Direct iodination of polyalkylbenzenes by the crossed Jacobsen reaction, COA of Formula: C10H13I, the main research area is .
cf. CA 60, 6732f. Slow, simultaneous addition of H2SO4 and o-MeOC6H4I (I) to a stirred polyalkylbenzene (II), or its solution in cyclohexane (III), the mixture stirred some time and poured into H2O, and the organic material separated, washed with aqueous NaHSO3, and worked up by fractional distillation (if liquid hydrocarbon) or chromatography on Al2O3 (if solid hydrocarbon) gave a polyalkyliodobenzene (IV). Thus, 24.3 g. p-(iso-Pr)2C6H4 (V) at 35-40° treated, over 1.5 hrs., with 23.4 g. I and 15 g. H2SO4, stirring continued 4 hrs., and the mixture poured into H2O and worked up gave 13.8 g. V, 7.1 g. mixture of I and a dealkylated iodo compound, and 6.0 g. 2,5-(isoPr)2C6H3I, b22 143-6°. Similarly were prepared (II, g. II, hrs. stirring, reaction temperature, IV, g. IV, and m.p. or b.p./mm. IV given): p-(tert-Bu)2C6H4, 3.7 (in 25 ml. III, 3, 30-3°, 2,5-diiodo-1,4-di-tert-butylbenzene (?), –, 49-50°; 1,2,4-Me3C6H3, 12.0, –, –, monoiodo product, 14.5, 121-5°/17-18; 1,3,5-Et3C6H3, 24.3, overnight, 30-2°, 2,4,6-Me3C6H2I, 17.1, 169-70°/31; 1,3,5-(iso-Pr)3C6H3, 20.4, 3 (then left overnight), 35-8°, 2,4,6-(iso-Pr)3C6H2I, 5.9, 173-5°/28; 1,2,4,5-Me4C6H2, 4.0, 4, 30-5°, 2,-3,5,6-Me4C6HI, 5.2, 80-1°; 1,2,4,5-Et4C6H2, 28.5, 4, 30-3°, 2,3,5,6-Et4C6HI, 13.5, 186-8°/26; Me5C6H, 7.4 (in 10 ml. III), 4, 34-6°, Me5C6I, 7.9, 141-2°. 1,2,4,5-(iso-Pr)4C6H2 did not react under these conditions.
Bulletin of the Chemical Society of Japan published new progress about Iodination. 2100-25-6 belongs to class iodides-buliding-blocks, name is 3-Iodo-1,2,4,5-tetramethylbenzene, and the molecular formula is C10H13I, COA of Formula: C10H13I.
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com