New, Efficient Synthesis ofα-Chloroketones Using SiCl4/Urea–Hydrogen Peroxide or SiCl4/Iodosylbenzene Reagent Systems

El-Ahl, A. A. S.; Elbeheery, Akram H.; Amer, F. A.

doi:10.1080/00397911.2010.487173

Cited by 11 publications

(6 citation statements)

References 16 publications

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“…679 mg (88%); yellow solid; mp 55–56 °C (lit . mp 53–55 °C); 1 H NMR (300 MHz, CDCl 3 ) δ 8.01–7.97 (m, 2H), 7.67–7.62 (m, 1H), 7.56–7.50 (m, 2H), 4.74 (s, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ 191.1, 134.2, 134.0, 128.9, 128.5, 46.1.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…1.04 g (88%); white solid; mp 119–120 °C (lit . mp 116 °C); 1 H NMR (300 MHz, CDCl 3 ) δ 7.85 (d, J = 8.7 Hz, 2H), 7.67 (d, J = 8.7 Hz, 2H), 4.68 (s, 2H); 13 C NMR (75 MHz, CDCl 3 ) δ 190.3, 132.9, 132.3, 130.0, 129.4, 45.6.…”

Section: Experimental Sectionmentioning

confidence: 99%

“…832 mg (90%); light yellow solid; mp 97–98 °C (lit . mp 98 °C); 1 H NMR (300 MHz, CDCl 3 ) δ 7.96 (d, J = 9.0 Hz, 2H), 6.98 (d, J = 9.0 Hz, 2H), 4.67 (s, 2H), 3.90 (s, 3H); 13 C NMR (75 MHz, CDCl 3 ) δ 189.7, 164.2, 130.9, 127.2, 114.1, 55.6, 45.7.…”

Section: Experimental Sectionmentioning

confidence: 99%

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Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

et al. 2016

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A configurationally simple and robust semibatch apparatus for the in situ on-demand generation of anhydrous solutions of diazomethane (CH2N2) avoiding distillation methods is presented. Diazomethane is produced by base-mediated decomposition of commercially available Diazald within a semipermeable Teflon AF-2400 tubing and subsequently selectively separated from the tubing into a solvent- and substrate-filled flask (tube-in-flask reactor). Reactions with CH2N2 can therefore be performed directly in the flask without dangerous and labor-intensive purification operations or exposure of the operator to CH2N2. The reactor has been employed for the methylation of carboxylic acids, the synthesis of α-chloro ketones and pyrazoles, and palladium-catalyzed cyclopropanation reactions on laboratory scale. The implementation of in-line FTIR technology allowed monitoring of the CH2N2 generation and its consumption. In addition, larger scales (1.8 g diazomethane per hour) could be obtained via parallelization (numbering up) by simply wrapping several membrane tubings into the flask.

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Section: Experimental Sectionmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

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Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

et al. 2016

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“…Both Tajbakhsh and Heravi illustrated that 1,4-diazabicyclo[2,2,2]octane (DABCO) can be employed as a halogenation agent ( Scheme 46 ) [ 125 , 126 ]. Heravi and co-workers used tetrameric DABCO-bromine (TBD) supported on silica or alumina to efficiently mediate the α-bromination of four aromatic ketones in good yields.…”

Section: Direct α-Halogenation Of Aryl Ketonesmentioning

confidence: 99%

Synthetic Access to Aromatic α-Haloketones

et al. 2022

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α-Haloketones play an essential role in the synthesis of complex N-, S-, O-heterocycles; of which some exhibit a remarkable biological activity. Research further illustrated that α-bromo-, α-chloro-, and α-iodoketones are key precursors for blockbuster pharmacological compounds. Over the past twenty years, substantial advances have been made in the synthesis of these industrially relevant building blocks. Efforts have focused on rendering the synthetic protocols greener, more effective and versatile. In this survey, we summarised and thoroughly evaluated the progress of the field, established in the past two decades, in terms of generality, efficacy and sustainability.

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“…α,α‐Dihaloketones can be transformed into biologically active heterocyclic compounds and can act as useful building blocks for valuable organic compounds However, α,α‐dichloroketones have been less frequently employed as a starting material in organic synthesis because convenient methods for their preparation have not been well explored. As a classical method, α‐chlorination of ketones has been adopted by using chlorinating reagents such as Cl 2 , sulfuryl chloride, ammonium salts of tetrachloroiodate, SiCl 4 /PhIO, and CuCl 2 (Scheme a). These methods, however, require high temperature or harsh conditions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of α,α‐Dichloroketones through Sequential Reaction of Decarboxylative Coupling and Chlorination

et al. 2018

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2,2‐Dichloro‐1,2‐diarylethanones were synthesized from diarylalkynes and trichloroisocyanuric acid. The reaction was conducted in CH3CN/H2O at room temperature for 12 h. In addition, the desired 2,2‐dichloro‐1,2‐diarylethanones could be prepared from aryl bromides and propiolic acid through sequential Pd‐catalyzed decarboxylative coupling and chlorination. This method showed moderate to good yields and good tolerance toward functional groups such as chlorides, bromides, aldehydes, and ketones.

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New, Efficient Synthesis ofα-Chloroketones Using SiCl₄/Urea–Hydrogen Peroxide or SiCl₄/Iodosylbenzene Reagent Systems

Cited by 11 publications

References 16 publications

Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

Laboratory-Scale Membrane Reactor for the Generation of Anhydrous Diazomethane

Synthetic Access to Aromatic α-Haloketones

Synthesis of α,α‐Dichloroketones through Sequential Reaction of Decarboxylative Coupling and Chlorination

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