3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Synthetic Route of C8H5IS
Preparation of 3-arylthianaphthenes was written by Schuetz, Robert D.;Ciporin, Leon. And the article was included in Journal of Organic Chemistry in 1958.Synthetic Route of C8H5IS This article mentions the following:
The synthesis of 3,3′-bithianaphthyl (I) was accomplished by using the Ullmann reaction with 3-iodothianaphthene (II). Preparation of 3-phenylthianaphthene (III) and 3-(1-naphthyl)thianaphthene (IV) was successfully realized by the reaction of 3-thianaphthenylmagnesium bromide (V) with the appropriate cyclic ketone followed by hydrolysis, dehydration, and dehydrogenation. Five previously unreported ο-aroyl-p-chlorophenyl Me sulfides (Va) were prepared by Friedel-Crafts acylation of p-ClC6H4SMe (VI) and the yields in the acylation reactions were correlated with the amount of steric hindrance involved in the formation of the sulfides. The ring closure with ClCH2CO2H (VII) of 3 of Va was carried out to yield the corresponding 5-chloro-3-aryl-2-thianaphthenecarboxylic acids (VIIa) which were previously unknown. Thianaphthene and iodine gave II. II (0.50 g.) heated to 150°, during 20 min. the temperature raised gradually to 270° with addition of 2.5 g. Cu bronze, the temperature kept 2 hrs. at 270-80°, the cooled mass extracted with cold CHCl3, and evaporated gave 0.2 g. polymeric substance, m. 258-9° (C6H6). The residue from the CHCl3 extraction extracted 30 hrs. with hot CHCl3 and filtered gave 0.4 g. crude I, m. above 370° (C6H6). V gave 3-(1-cyclohexenyl)thianaphthene (VIII) and 3-(3,4-dihydro-1-naphthyl)thianaphthene (IX) and aromatization of VIII and IX was accomplished as follows. VIII or IX heated at 240-50° with the required amount of S until the H2S evolution ceased, the cooled mass dissolved in hot C6H6, the unchanged S removed, the filtrate washed with 10% Na2SO3, and dried gave a residue which sublimed at 230-40°/10 mm. gave the appropriate III and IV. III m. 172-3°, 17% yield, and IV m. 90-2°, 38% yield. p-ClC6H4SH (100 g.) in 350 ml. 10% NaOH treated during 0.5 hr. with 177 g. Me2SO4, an addnl. 150 ml. 10% NaOH added to maintain alkalinity, extracted with Et2O, the extract dried, evaporated, and the crude product distilled gave 94.7 g. VI, b14 107°, n20D 1.5997. Va were prepared as follows. Equimolar amounts of the aroyl chloride and anhydrous AlCl3 brought together at a temperature 5° higher than the m.p. of the aroyl chloride, 1/6 to 1/3 the required amount of VI added dropwise during 0.5 hr., the mixture held at the original temperature 10 hrs., the cooled complex poured into dilute HCl and ice, extracted with Et2O, the Et2O washed with 10% NaOH, dried, the drying agent removed, and the residue distilled gave Va. The following Va were thus obtained (R in the ο-COR group, m.p., and % yield given): Ph, 101-3°, 38; α-naphthyl, 115-17°, 4; β-naphthyl, 120-1°, 25; α-thienyl, 77-8°, 35; ο-carboxyphenyl, 183-5°, 13. VI (10 g.), 4.6 g. ο-C8H4(CO)2O, and 10.5 g. anhydrous AlCl3 kept 4 hrs. at 80°, the mixture cooled, decomposed with H2O, steam distilled to remove unreacted VI, the residue extracted with hot CHCl3 to remove the anhydride, and the CHCl3 evaporated gave a solid residue which washed with ligroine and recrystallized gave Va (R = ο-carboxyphenyl). VIIa were prepared as follows. The Va added to 4-6 moles excess VII, the solution kept 10-72 hrs. at 80-130°, and H2O added precipitated the VIIa which was collected and recrystallized from C6H6. The VIIa so obtained were (aryl group, m.p., and % yield given): Ph, 263-5°, 16; α-thienyl, 267-8°, 53; ο-carboxyphenyl, 282-4°, 61. In the experiment, the researchers used many compounds, for example, 3-Iodobenzo[b]thiophene (cas: 36748-88-6Synthetic Route of C8H5IS).
3-Iodobenzo[b]thiophene (cas: 36748-88-6) belongs to iodide derivatives. Organic iodides can be alkyl, alkenyl, or alkynyl, and all of them are very reactive toward with many kinds of nucleophiles. Polyiodoorganic compounds are sometimes employed as X-ray contrast agents, in fluoroscopy, a type of medical imaging. This application exploits the X-ray absorbing ability of the heavy iodine nucleus.Synthetic Route of C8H5IS
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com