Halogenation. XXIII. Halogenation of fluorobenzene, o-, m- and p-fluorotoluenes was written by Varma, P. S.;Venkat Raman, K. S.;Nilkantiah, P. M.. And the article was included in Journal of the Indian Chemical Society in 1944.Product Details of 452-62-0 This article mentions the following:
PhF (I) (10 cc.) treated with 1 mol. Cl (II) and 0.5 g. Fe powder, with occasional shaking, yields p-chlorofluorobenzene (III), b. 130°, while with 2 mols. II, it gives III and a mixture of 2,4- and 3,4-dichlorofluorobenzenes, b. 169-75°. The same mixture is obtained from III with 1 mol. II. FC6H4Br (15 g.), 1 g. Fe powder and 4.5 cc. Br (IV), yield, upon refluxing for 8 hrs., 5.8 g. 3,4-dibromofluorobenzene, needles (alc.), m. 69°, and 2,4-dibromofluorobenzene (V), b32 103-5°, b756 214-16°. I, iodine and NaNO2 in CCl4 refluxed for 4 hrs. after adding fuming H2SO4 dropwise during 1 hr., give p-iodofluorobenzene (VI), light brown oil, b758 178-81°. Similarly, m-fluorotoluene (VII) yields 3-fluoro-6-iodotoluene, b9 138-9° and 3-fluoro-4-iodotoluene, b9 138-9°, and o-fluorotoluene (VIII) gives 2-fluoro-5-iodotoluene (IX), light yellowish, b8 85°, and 2-fluoro-6-iodotoluene (X), b8 114-16°. VI, upon refluxing at 200-20° for 6 hrs. with Cu bronze, gives 4,4′-difluorobiphenyl, m. 89°. II (1.3 mols.) bubbled through VIII and Fe powder for 5-6 hrs. yields X, b752 151-2°, which yields the corresponding benzoic acid, m. 159°, upon oxidation, and a product (XI), b752 157-9° found to be identical with the product (XII) obtained by treating diazotized 2-fluoro-5-aminotoluene (XIII) with CuCl. Both XI and XII give 2-fluoro-5-chlorobenzoic acid, m. 168°, upon oxidation. IV in CCl4 added dropwise, under cooling, to VII in CCl4, in the presence of Fe powder, yields, after standing overnight, 3-fluoro-4-bromotoluene, b756 169°, and 3-fluoro-6-bromotoluene, b756 177°, the latter giving 3-fluoro-6-bromobenzoic acid, needles, m. 151°, upon oxidation with alk. KMnO4. Similarly, p-FC6H4Me yields 4-fluoro-3-bromotoluene, b757 174-7°, and 4-fluoro-3-bromobenzoic acid, white, m. 156°. VIII treated with fuming HNO3 gives 2-fluoro-5- (XIV) and -6-nitrotoluenes. Reduction of XIV yields 2-fluoro-5-aminotoluene, brownish black, b9 85-6° (HCl salt, m. 220° (decomposition)), which upon diazotization and treatment with KI yields IX, b9 86-7°. 2-Fluoro-6-aminotoluene gives by the same process X, b9 117°. o-, m- and p-Fluorobenzyl iodides, b8 91°, b12 98° and b9 102-3°, resp., were obtained by refluxing the corresponding benzyl chloride or bromide with KI in acetone for 4-5 hrs. VII treated with 2 mols. II, followed by heating for 6 hrs. on a sand bath, gives m-fluorobenzyl chloride, b756 176°, and m-fluorobenzal chloride, b756 195-7°, while with IV it gives m-fluorobenzal bromide, b8 108-10°. Similarly, o- and m-fluorobenzal chlorobromides, b7 109-10°, and b756 228-30°, b9 111-13°, resp., were obtained from the corresponding fluorobenzyl bromide. In the experiment, the researchers used many compounds, for example, 3-Bromo-4-fluorotoluene (cas: 452-62-0Product Details of 452-62-0).
3-Bromo-4-fluorotoluene (cas: 452-62-0) belongs to organobromine compounds. Most of the natural organobromine compounds are produced by marine organisms, and several brominated metabolites with antibacterial, antitumor, antiviral, and antifungal activity have been isolated from seaweed, sponges, corals, molluscs, and others. One prominent application of synthetic organobromine compounds is the use of polybrominated diphenyl ethers as fire-retardants, and in fact fire-retardant manufacture is currently the major industrial use of the element bromine.Product Details of 452-62-0
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary