5876-90-4

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 7726-95-6 bromine 
• 871893-76-4 2,4,6-trimethoxy-isophthalic acid 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 106-42-3 para-xylene 
• 570-02-5 2,4,6-trimethoxybenzoic acid 
• 186581-53-3 diazomethane 
• 84743-75-9 2,4-dibromo-1,3,5-trihydroxybenzene 

Downstream Products

• 92670-03-6 2,4-bis(trimethylsilyl)-1,3,5-trimethoxybenzene 
• 621-23-8 1,2,3-trimethoxybenzene 
• 60077-70-5 1,3-dibromo-5-(2,3-dibromo-4,5-dimethoxybenzyl)-2,4,6-trimethoxybenzene 

Relevant academic research and scientific papers

HALOGENATED PHLOROGLUCINOLS FROM RHABDONIA VERTICILLATA

Six bromo- and/or chloro- derivatives of phloroglucinol have been obtained from the red alga Rhabdonia verticillata.Key Word Index - Rhamdonia verticillata; Rhambdoniaceae; halogenated phenols; bromo- and chlorophloroglucitols.

Oxidative bromination reactions in aqueous media by using Bu4NBr/TFA/H2O2 system

Metal-free oxidative bromination reactions in aqueous media were performed using tetrabutylammonium bromide, trifluoroacetic acid, and hydrogen peroxide under mild conditions. Oxidative bromination reaction of alkenes was found to afford the corresponding vic-bromides. Furthermore, this oxidative bromination system is applicable to the oxidative bromination of alkynes, arenes, and 3,4-dihydronaphthalen-1(2H)-one. A gram-scale bromination reaction was also performed successfully.

Transition metal-free protodecarboxylation of electron rich aromatic acids under mild conditions

A mild and practical method for the transition metal-free protodecarboxylation of aromatic acids using readily available and safe sodium persulfate as initiator was described. This environment-friendly decarboxylation approach was performed at 60 °C in ethanol and could easily scale up to the gram level with a good yield. In Particular, the tandem reactions of decarboxylation and halogenation were achieved by the addition of the corresponding halogenating reagents to the reaction system.

Photocatalytic Selective Bromination of Electron-Rich Aromatic Compounds Using Microporous Organic Polymers with Visible Light

Pure organic, heterogeneous, metal-free, and visible light-active photocatalysts offer a more sustainable and environmentally friendly alternative to traditional metal-based catalysts. Here we report a series of microporous organic polymers containing photoactive conjugated organic semiconductor units as heterogeneous photocatalysts for a visible-light-promoted, highly selective bromination reaction of electron-rich aromatic compounds using HBr as a bromine source and molecular oxygen as a clean oxidant. Via a simple Friedel-Crafts alkylation reaction, the microporous organic polymers were obtained by cross-linking of organic semiconductor compounds with defined valence and conduction band positions. The utilization of the simply prepared porous polymer-based photocatalytic systems opens new opportunities toward a sustainable and efficient material design for catalysis.

Effective bromo and chloro peroxidation catalysed by tungsten(vi) amino triphenolate complexes

Amino triphenolate tungsten(vi) complexes have been prepared and they proved to be efficient catalysts in haloperoxidation reactions using hydrogen peroxide as a terminal oxidant and inorganic sources of halides. In particular, interesting results have been obtained in the challenging chloroperoxidation reactivity (catalyst loading down to 0.05% with TONs up to 900). A comparison among three different metal complexes bearing the same ligand (vanadium(v), molybdenum(vi) and tungsten(vi)) showed much better performances of the last complex both on bromo and chloro peroxidations.

Cross-Dehydrogenative-Coupling of Alkoxybenzenes with Toluenes: Copper(II) Halide Mediated Tandem Halo/Benzylation of Arenes

A cross-dehydrogenative-coupling of alkoxybenzenes and toluenes with concomitant halogenation is reported. Conditions employed were the use of stoichiometric copper halide salts and dialkylperoxides to afford a range of bromoalkoxydi- and triarylmethanes. Preliminary mechanistic studies suggest that the in situ production of haloarenes (or dihaloarenes) followed by a copper-mediated coupling of a benzylic radical is operational.

Efficient and Practical Oxidative Bromination and Iodination of Arenes and Heteroarenes with DMSO and Hydrogen Halide: A Mild Protocol for Late-Stage Functionalization

An efficient and practical system for inexpensive bromination and iodination of arenes as well as heteroarenes by using readily available dimethyl sulfoxide (DMSO) and HX (X = Br, I) reagents is reported. This mild oxidative system demonstrates a versatile protocol for the synthesis of aryl halides. HX (X = Br, I) are employed as halogenating reagents when combined with DMSO which participates in the present chemistry as a mild and inexpensive oxidant. This oxidative system is amenable to late-stage bromination of natural products. The kilogram-scale experiment (>95% yield) shows great potential for industrial application.

Practical and metal-free electrophilic aromatic halogenation by interhalogen compounds generated in situ from N-halosuccinimide and catalytic TMSCL

Halomonochloride compounds (ClCl, BrCl, ICl) generated in situ from N-halosuccinimide and catalytic chlorotrimethylsilane (TMSCl, 0.1 equiv) can efficiently halogenate aromatic compounds to give halogenated products in good to excellent yields and selectivities. The reaction can be carried out at room temperature or at lower temperatures, requires only one hour, is practical to apply to a wide range of substrates, and provides a simple access to a variety of haloarene compounds. Georg Thieme Verlag Stuttgart New York.

Oxidative bromination reaction using vanadium catalyst and aluminum halide under molecular oxygen

The vanadium-catalyzed oxidative bromination reaction of arenes, alkenes, and alkynes was performed in the presence of AlBr3 to provide an alternative method for conventional bromination using hazardous bromine. The catalytic cycle is formed under molecular oxygen, which is more advantageous to vanadium bromoperoxidase (VBrPO) requiring hydrogen peroxide as a terminal oxidant.

Vanadium-catalyzed oxidative bromination promoted by Br?nsted acid or Lewis acid

The oxidative bromination of arenes was induced by a vanadium catalyst in the presence of a bromide salt and a Br?nsted acid or a Lewis acid under molecular oxygen, which provides an eco-friendly bromination method as compared with a conventional bromination one with bromine. This catalytic reaction could be applied to the bromination of alkenes and alkynes to give the corresponding vic-bromides. Use of aluminum halide as a Lewis acid in place of a Br?nsted acid was demonstrated to provide a more practical protocol for the oxidative bromination. From ketones, α-bromination products were obtained. AlBr3 was found to serve as both a bromide source and a Lewis acid to induce the bromination smoothly. 51V NMR experiment showed that this catalytic bromination is likely to depend on the redox cycle of a vanadium catalyst under molecular oxygen.