Rearrangement of the bromine atom in the demethylation of bromomethoxybenzoic acid. IV. 2-Bromoanisic acid and 3-bromoanisic acid was written by Tomita, Masao;Fujitani, Kazuyoshi. And the article was included in Yakugaku Zasshi in 1956.Related Products of 82380-17-4 This article mentions the following:
2,4-Br(MeO)C6H3CO2H (XI), needles, m. 197-8°, was synthesized from 4-O2NC6H4Me or p-cresol as a raw material. Nitration of 3-BrC6H4OH gave 3,4-Br(O2N)C6H3OH, m. 125-31°, which was reduced to 3,4-Br(H2N)C6H3OH, m. 151°; this was diazotized and treated with CuCN yielding 2,4-Br(HO)C6H3CN (XII), m. 151°. XI (0.5 g.), 15 ml. PhCl, and 2 g. AlCl3 heated 1.5 hrs. on a water bath and the product poured on ice and extracted with Et2O gave 0.3 g. 2,4-Br(HO)C6H3CO2H (XIII), needles, m. 206-8° (from water); the m.p. of XIII given as 151° by Hodgson and Jenkinson (cf. C.A. 22,949) was confirmed to be the m.p. of XII. XI (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated 5 hrs. at 130° and 2 hrs. at 150°, the product concentrated, neutralized with NaHCO3 to remove the acidic substance, extracted with Et2O, stirred with NaOH, and the NaOH layer acidified with HCl and extracted with Et2O gave 3-BrC6H4OH (benzoate, m. 84-5°) and a small amount of XIII, m. 206-8°. XI (0.5 g.) and 6 ml. HCl-AcOH in a sealed tube heated 12 hrs. at 150° gave 0.45 g. XI. 2,4-Br(MeO)C6H3CO2Me (XIV), plates, m. 29°, (1 g.) and 7 ml. HBr-AcOH in a sealed tube heated and the product treated as usual gave 3-BrC6H4OH. Similarly, 3,4-Br(MeO)C6H3CO2H gave 3,4-Br(HO)C6H3CO2H, m. 106-7°. 3,4-Br(MeO)C6H3CO2Me (0.5 g.) gave 0.3 g. 3,5,4-Br2(HO)C6H2CO2H, m. 253-7° (decomposition), and 0.1 g. 3,4-Br(HO)C6H3CO2H, m. 175-7° (Me ester, m. 107°). In the experiment, the researchers used many compounds, for example, 2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4Related Products of 82380-17-4).
2-Bromo-4-hydroxybenzonitrile (cas: 82380-17-4) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Nitrile groups in organic compounds can undergo a variety of reactions depending on the reactants or conditions. A nitrile group can be hydrolyzed, reduced, or ejected from a molecule as a cyanide ion.Related Products of 82380-17-4
Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts