The action of sodium methoxide on some derivatives of o-dichlorobenzene was written by Kraay, G. M.. And the article was included in Diss. Amsterdam in 1926.Quality Control of 2-Chloro-5-iodophenol This article mentions the following:
The derivatives studied represent o-C6H4Cl2 in which a p-H atom is replaced by F, Cl, Br, I, NO2, SO3H, Me, CO2H, NH2, OH, NO, CN, CHO and COPh. These substances were treated with NaOMe in MeOH at 180° and in most cases the products isolated and identified in order to determine where the replacement occurred. It appears that a halogen is first replaced by OMe to yield an anisole, which then reacts with a 2nd mol. of NaOMe giving the Na salt of a phenol and Me2O. New substances of the above type are 3,4-dichlorofluorobenzene (I), b. 171°, prepared in 88% purity by treating the diazotized Cl2C5H3NH2 with 55% HF, distilling with steam and fractionating several times; 3,4-dichloroiodobenzene (II), m. 30.5°, in 83% yield by the Sandmeyer reaction with KI; 3,4-dichlorobenzonitrile (III), m. 72.1°, in 57% yield by the Sandmeyer reaction with CuCN; 3,4-dichloronitrosobenzene (IV), m. 88°, by reduction of the corresponding nitro derivative with NaSH to 3,4-dichlorophenylhydroxylamine (73% yield), m. 75° (decomposition), which readily oxidizes in the air to 3,3′,4,4′-tetrachloroazoxybenzene (V), m. 139-9.5°, and then oxidation with K2Cr2O7 (yield 50%); and 3,4-dichlorobenzyl alc. (VI), m. 38°, from the corresponding aldehyde by the Cannizzaro reaction. New products obtained by treatment of p-substituted o-C6H4Cl2 with NaOMe are 3-hydroxy-4-chlorotoluene (VII), m. 46°, from the Cl2C6H3Me; 2-chloro-5-bromophenol (VIII), m. 57°, from the C6H3Cl2Br; and 2-chloro-5-iodophenol (IX), m. 56.5°, from II. VIII was also prepared by diazotization of 2,5-ClBrC6H3NH2. 2-Chloro-5-iodonitrobenzene, m. 74.5°, was prepared in 86% yield by treating the diazotized Cl(O2N)C6H3NH2 with KI; reduction of this with TiCl2 gave 84% of 2-chloro-5-iodoaniline, m. 61.5°, and this in turn when treated with HNO2 gave IX. VII was also prepared in 78% yield from the chlorotoluidine and HNO2. In the above 3 phenols the 3-Cl had been replaced by OH. The 2 following reactions carried out in the same manner showed a replacement elsewhere; Iâ?,4-Cl2C6H3OH, 3,4-Cl2C6H3SO3Hâ?,4-Cl(HO)C5H3SO3H. In the case of 3,4-Cl2C6H3OH no reaction occurred, III gave unidentified products of saponification, IV became reduced to V, 3,4-Cl2C6H3COPh was recovered for the most part unchanged, and 3,4-Cl2C6H3CHO probably underwent the Cannizzaro reaction. Selective replacements of the halogens are discussed from the standpoint of polarity. In the experiment, the researchers used many compounds, for example, 2-Chloro-5-iodophenol (cas: 289039-26-5Quality Control of 2-Chloro-5-iodophenol).
2-Chloro-5-iodophenol (cas: 289039-26-5) belongs to iodide derivatives. Iodide-containing intermediates are common in organic synthesis, because of the easy formation and cleavage of the C–I bond. Organoiodine lubricants can be used with titanium, stainless steels, and other metals which tend to seize up with conventional lubricants: organoiodine lubricants can be used in turbines and spacecraft, and as a cutting oil in machining.Quality Control of 2-Chloro-5-iodophenol
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com