Halogenation of Aromatic Methyl Ketones Using Oxone® and Sodium Halide

Kim, Eun-Hoo; Koo, Bon-Suk; Song, Choong Eui; Lee, Kee‐Jung

doi:10.1081/scc-100107011

Cited by 36 publications

(6 citation statements)

References 23 publications

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“…[16] Interestingly, we also found a fast, highly selective and high yielding synthesis of 4-halogenated acetylpyrrole from 2-acetylpyrrole, by using oxone and sodium halide in methanol/water mixtures (Scheme 2). [17] This result contrasts with the reported regiochemistry of this reaction. [17] It was observed that coupling constants recorded in the 1 H NMR spectra of these systems are rather small, which, when combined with metacoupling and NH-coupling, complicates the assignment of the structure (see the Supporting Information).…”

Section: Synthesis Of 3-chloro-bodipy Dyescontrasting

confidence: 70%

“…[17] This result contrasts with the reported regiochemistry of this reaction. [17] It was observed that coupling constants recorded in the 1 H NMR spectra of these systems are rather small, which, when combined with metacoupling and NH-coupling, complicates the assignment of the structure (see the Supporting Information).…”

Section: Synthesis Of 3-chloro-bodipy Dyescontrasting

confidence: 70%

See 1 more Smart Citation

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

et al. 2011

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Starting from appropriately halogenated acylpyrroles, a wide range of reactive 4,4‐difluoro‐4‐bora‐3a,4a‐diaza‐s‐indacene (BODIPY) derivatives can be obtained. The fluorescent dyes display excellent reactivity in nucleophilic aromatic substitution, transition‐metal‐catalyzed cross‐coupling and copper‐catalyzed cycloaddition to azides (click chemistry). The spectral properties of the starting and final difluoroboron dipyrromethenes are discussed as a function of their structure.

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Section: Synthesis Of 3-chloro-bodipy Dyescontrasting

confidence: 70%

Section: Synthesis Of 3-chloro-bodipy Dyescontrasting

confidence: 70%

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

et al. 2011

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“…Like other green oxidants such as O 2 and H 2 O 2 [ 5 ], peroxymonosulfate (PMS, Oxone ® ) has been widely used: (1) in the academia to develop new synthetic protocols [ 6 ]; (2) in pharmaceutical companies to promote oxidative stress testing of active pharmaceutical ingredients (API) to predict their degradation [ 7 ]; and (3) in hypersaline industrial wastewaters to remove organic contaminants [ 8 , 9 , 10 ]. This safe, sustainable, and inexpensive oxidant has shown extraordinary reactivity with alkaline metal halide salts [ 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 ] and with hydrogen halides (HCl, HBr and HI) [ 28 , 29 , 30 ].…”

Section: Introductionmentioning

confidence: 99%

Selective Oxidation of Clopidogrel by Peroxymonosulfate (PMS) and Sodium Halide (NaX) System: An NMR Study

Krake

Baumann

2021

Molecules

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A selective transformation of clopidogrel hydrogen sulfate (CLP) by reactive halogen species (HOX) generated from peroxymonosulfate (PMS) and sodium halide (NaX) is described. Other sustainable oxidants as well as different solvents have also been investigated. As result of this study, for each sodium salt the reaction conditions were optimized, and four different degradation products were formed. Three products were halogenated at C-2 on the thiophene ring and have concomitant functional transformation, such as N-oxide in the piperidine group. A halogenated endo-iminium product was also observed. With this condition, a fast preparation of known endo-iminium clopidogrel impurity (new counterion) was reported as well. The progress of the reaction was monitored using nuclear magnetic resonance spectroscopy as an analytical tool and all the products were characterized by 1D-, 2D-NMR and HRMS.

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“…The most commonly used reagents for a-bromination of ketones include molecular bromine [20], N-bromosuccinimide (NBS) [21]. Recently, various methods have been reported using NBS-NH 4 OAc [22], NBS-photochemical [23], NBS-PTSA [24], NBS-silica supported sodium hydrogen sulphate [25], NBS-Amberlyst-15 [26], NBS-Lewis acids [27], NBS-ionic liquids [28], MgBr 2 -(hydroxy(tosyloxy)iodo)benzene-MW [29], N-methylpyrrolidin-2-one hydrotribromide (MPHT) [30], (CH 3 ) 3 SiBr-KNO 3 [31], BDMS, NaBr [32].…”

Section: Synthesis Of Five-membered Heterocylces From Phenacyl Halidementioning

confidence: 99%

Phenacyl Bromide: An Organic Intermediate for Synthesis of Five- and Six-Membered Bioactive Heterocycles

Jangid¹,

Dhadda²

2020

Heterocycles - Synthesis and Biological Activities

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An environmentally friendly, economic synthetic protocol was advanced for synthesis of biologically and pharmacologically vital five-and six-membered heterocycles containing nitrogen, sulphur and oxygen as heteroatom. A series of thiazole derivatives was prepared by the reaction of substituted phenacyl halides and phenyl thiourea in the presence of TiO 2 nanoparticles (NPs) as nanocatalyst in DCM. Similarly, another series of six-membered heterocyclic compounds were synthesized by the reaction of phenacyl halides with phenylenediamine, 2-aminophenol, 2-aminobenzenethiol to produce corresponding products (1,4-quinoxaline, benzoxazine, benzothiazine) under catalytic effect of TiO 2 nanocatalyst. Analytical and spectral (FTIR, 1 H and 13 C NMR and SEM) techniques were employed for the structural elucidation of the synthesized compounds.

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Halogenation of Aromatic Methyl Ketones Using Oxone® and Sodium Halide

Cited by 36 publications

References 23 publications

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

2‐ and 3‐Monohalogenated BODIPY Dyes and Their Functionalized Analogues: Synthesis and Spectroscopy

Selective Oxidation of Clopidogrel by Peroxymonosulfate (PMS) and Sodium Halide (NaX) System: An NMR Study

Phenacyl Bromide: An Organic Intermediate for Synthesis of Five- and Six-Membered Bioactive Heterocycles

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