95667-98-4

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 124-63-0 methanesulfonyl chloride 
• 119-36-8 methyl salicylate 

Downstream Products

• 93-58-3 benzoic acid methyl ester 
• 6587-24-2 methyl 2-cyanobenzoate 
• 39732-01-9 2-(2-furyl)benzoic acid methyl ester 
• 55676-77-2 dimethyl [1,1'-biphenyl]-2,4'-dicarboxylate 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide-new enol nucleophile in three-component interaction with benzaldehydes and active methylene nitriles

The reactivity of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide was studied in multicomponent type reactions for the first time, namely, in a three-component interaction with active methylene nitriles and aromatic aldehydes in order to construct condensed 2-amino-4H-pyran derivatives. The reaction outcome strongly depended on the nature of an active methylene nitrile and an arenecarbaldehyde. Application of malononitrile resulted in novel 2-amino-4-aryl-4H-pyrano[3,2-c][1,2]benzoxathiine-3-carbonitrile 5,5-dioxides in most cases, whereas the utilization of ethyl cyanoacetate resulted in a complex mixture of products. In the last case, three different products were isolated depending on the arenecarbaldehyde used, namely ethyl 2-amino-4-aryl-4H-pyrano[3,2-c][1,2]benzoxathiine-3-carboxylate 5,5-dioxides, ethyl 2-cyano-3-arylacrylates, and salts of 3,3′-(arylmethylene)bis(4-hydroxybenzo[e][1,2]oxathiine 2,2-dioxides). Attempts to obtain separately ethyl 2-amino-4-aryl-4H-pyrano[3,2-c][1,2]benzoxathiine-3-carboxylate 5,5-dioxides enabled us to propose reaction pathways leading to these products. The salts were obtained for the first time. The preparative method for the synthesis of triethylammonium salts of 3,3′-(arylmethylene)bis(4-hydroxybenzo[e][1,2]oxathiine 2,2-dioxides) was proposed by the direct interaction of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide with arenecarbaldehydes. The application of ammonium acetate as a catalyst allowed us to synthesize 7-aryl-7,14-dihydrobenzo[5,6][1,2]oxathiino[4,3-b]benzo[5,6][1,2]oxathiino[3,4-e]pyridine 6,6,8,8-tetraoxides containing a novel heterocyclic system. These facts, combined with our past investigations, allowed us to assert that the reactivity of enol nucleophiles that include the COCH2SO2X fragment has not been reported previously.

Introduction of Aryl Fluorosulfates into the Realm of Catellani Reaction Substrates

Application of activated phenol fluorosulfates as substrates in a Pd/NBE mediated sequential alkylation-arylation, commonly known as a Catellani reaction, is presented. These substrates provide a level of complementarity to the commonly used aryl halides and, in combination with a plethora of existing Catellani reaction variations, enable even wider application of this powerful synthetic tool.

Late-Stage Aromatic C-H Oxygenation

Synthetic methods for oxidative aromatic C-O bond formation are sparse, despite their demand in metabolite synthesis for drug discovery and development. We report a novel methodology for late-stage C-O bond formation of arenes. The reaction proceeds with excellent functional group tolerance even for highly functionalized substrates. The resulting aryl mesylates provide access to potential human metabolites of pharmaceuticals, and may be used directly to install a C-F bond to block metabolic hotspots. A charge-transfer interaction between the reagent bis(methanesulfonyl) peroxide and the substrate arenes may be relevant for the chemoselective functionalization of arenes over other functional groups.

METHOD TO PREPARE PHENOLICS FROM BIOMASS

The present invention is directed to a method for preparing a final phenolic product from biomass comprising the steps of providing a furanic compound obtainable from biomass; reacting the furanic compound with a dienophile to obtain a phenolic compound; reacting the phenolic compound further to obtain the final phenolic product.

Neopentylglycolborylation of aryl mesylates and tosylates catalyzed by Ni-based mixed-ligand systems activated with Zn

(Chemical Presented) The mixed-ligand system NiCl2(dppp)/dppf is shown to be an effective catalyst for the neopentylglycolborylation of ortho-, meta-, and para-substituted electron-rich and electrondeficient aryl mesylates and tosylates. The ad

IMPROVED PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL FOR THE PREPARATION OF ZONISAMIDE

The invention relates to an improved process for the preparation of 1,2-benzisoxazole-3--methane sulfonates and a novel compound 4-oximino-2,3-dihydrobenzoxathiin-2, 2--dioxides. The 1,2-benzisoxazole-2-methane sulfonates and 4-oximino-2, 3--dihydrobenzoxathiin-2, 2-dioxides prepared by the processes of the present invention have the general formula (2) and (3) respectively . The compounds of the formulae (2) and (3) are important intermediates for the preparation of Zonisamide of the formula (1) (an anticonvulsant drug). The compounds of the formula (2) is prepared from hitherto unknown compound 4-oximino-2,3-dihydrobenzoxathiin-2, 2-dioxides of the formula (3) using strong bases with suitable solvents. The novel compounds of the formula (3) is prepared by the intramolecular Cyclocondensation of the compound of the formula (4) to get the compound of the formula (5) and subsequent reaction with hydroxylamine hydrochloride to get the novel intermediates of the formula (3). In the above mentioned formulae R1 to R4 - may be the same or different and represents hydrogen, alkyl, (with carbons, 2-5), chloro, bromo, S- alkyl, o- alkyl, NO2, N- Me2, CF3. and where X represents Na or K.

NiCl2(dppe)-Catalyzed Cross-Coupling of Aryl Mesylates, Arenesulfonates, and Halides with Arylboronic Acids

An investigation of the NiCl2(dppe)-, NiCl2(dppb)-, NiCl2(dppf)-, NiCl2(PCy3)2-, and NiCl2(PPh3)2- catalyzed cross-coupling of the previously unreported aryl mesylates, and of aryl arenesulfonates, chlorides, bromides, and iodides containing electron-withdrawing and electron-donating substituents with aryl boronic acids, in the absence of a reducing agent, is reported. NiCl2(dppe) was the only catalyst that exhibited high and solvent-independent activity in the two solvents investigated, toluene and dioxane. NiCl2(dppe) with an excess of dppe, NiCl 2(dppe)/dppe, was reactive in the cross-coupling of electron-poor aryl mesylates, tosylates, chlorides, bromides, and iodides. This catalyst was also efficient in the cross-coupling of aryl bromides and iodides containing electron-donating substituents. Most surprisingly, the replacement of the excess dppe from NiCl2(dppe)/dppe with excess PPh3 generated NiCl2(dppe)/PPh3, which was found to be reactive for the cross-coupling of both electron-rich and electron-poor aryl mesylates and chlorides. Therefore, the solvent-independent reactivity of NiCl2(dppe) provides an inexpensive and general nickel catalyst for the cross-coupling of aryl mesylates, tosylates, chlorides, bromides, and iodides with aryl boronic acids.

Process for the preparation of 2-(4-methylphenyl)-benzoic acid derivatives

A process for the preparation of 2-(4-methylphenyl)benzoic acid C1-6alkyl esters by reaction of a sulfonic derivative of formula wherein R is C1-6alkyl and R1is optionally perfluorinated C1-6alkyl or optionally substituted C1-6aryl, with a 4-methylphenylzinc halide.

Scope and limitation of the nickel-catalyzed coupling reaction between lithium borates and mesylates

Coupling reaction of aryl borates and mesylates derived from phenols and enols was studied. Mesylates with an electron-with-drawing group or ring were highly reactive at room temperature in the presence of NiCl2(PPh3)2 to furnish the coupling products in good yields.