72470-95-2Relevant articles and documents
Aryl Diazonium Salts: Powerful Arylating Agents for Catellani-Typeortho-Arylation
Fu, Ying,Guo, Liang-Liang,Zhang, Yu-Xia
supporting information, p. 17437 - 17444 (2021/12/02)
The Catellani reaction provides an efficient synthetic approach to polyfunctionalized arenes. However, the selectiveortho-arylating reagents employed in these reactions have been strictly limited to activated bromoarenes. As demonstrated in this work, aryl diazonium salts bearing both electron-donating and electron-withdrawing substituents, after in situ transformations with KI into the corresponding iodoarenes, were efficient arylating reagents for Catellani typeortho-arylation approaches.
Long-chain Phenols. Part 16. A Novel Synthesis of Homologous Orsellinic Acids and their Methyl Ethers
Durrani, Aziz A.,Tyman, John H. P.
, p. 1658 - 1666 (2007/10/02)
By the novel reaction of 3,5-dimethoxyfluorobenzene with n-alkyl-lithium compounds, followed by carbonation, homologous orsellinic acid dimethyl ethers (6-alkyl-2,4-dimethoxybenzoic acids) have been obtained.The reactions proceeded best with the homologues of methyl-lithium.These reactions are considered to occur by way of 3,5-dimethoxybenzyne. 2,4-Dimethoxyfluorobenzene did not form an aryne but gave 3-fluoro-2,6-dimethoxybenzoic acid instead.Decomposition with water of alkyl-lithium reaction mixtures from 3,5-dimethoxyfluorobenzene yielded 5-n-alkylresorcinol dimethyl ethers.Demethylaton of 6-alkyl-2,4-dimethoxybenzoic acids with boron trichloride proceeded partially and selectively to give the 6-alkyl-2-hydroxy-4-methoxybenzoic acids, and completely with aluminium chloride to give the homologous orsellinic acids.Boron tribromide was less effective, but readily gave the 5-alkyl resorcinols from the corresponding dimethyl ethers.
