Metal nitrate promoted highly regiospecific ortho–nitration of phenols: Application to the synthesis of nitroxynil. Issue 7 (18th April 2023)

• Record Type: Journal Article
• Authors: Iqbal, Zafar; Joshi, Asha; De, Saroj Ranjan
• Is Part Of: Synthetic communications. Volume 53:Issue 7/8(2023)
• Page Start: 557
• Page End: 567
• Publication Date: 2023-04-18
• Subjects: Cheap nitrating agents -- metal nitrates -- ortho-nitration -- phenol carbonates; Organic compounds -- Synthesis -- Periodicals; Chemistry, Organic; Synthesis; 547.205
• DOI: 10.1080/00397911.2023.2184270
• Languages: English
• ISSNs: 0039-7911

Abstract

Abstract: Highly regiospecific ortho –nitration of electronically diverse phenols is accomplished using Fe(NO3 )3 .9H2 O for electron–rich and Cu(NO3 )2 .6H2 O for electron–deficient phenols as the cheap nitrating agents. The reaction is carried out in CH3 CN at 90 °C under mild and neutral conditions where structurally diverse phenols afford exclusively ortho –nitration products in moderate to good yields with outstanding tolerance of functional groups. The synthetic application of this strategy was established by achieving the bioactive compound nitroxynil. Graphical Abstract: UF0001