70132-79-5

Upstream product

• 32250-86-5 2-[(2-chlorophenyl)methyl]-1,4-dimethylbenzene 
• 106-42-3 para-xylene 
• 609-65-4 o-chlorobenzoyl chloride 
• 22328-43-4 2,5-dimethylbenzoyl chloride 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 16537-16-9 2-chloro-benzoic acid tert-butyl ester 
• 118-91-2 ortho-chlorobenzoic acid 

Downstream Products

• 70132-80-8 3-(2,5-dimethyl-phenyl)-benzo[d]isothiazole 

Relevant academic research and scientific papers

Controlled photo-flow oxidative reaction (UV-FOR) platform for ultra-fast phthalide and API synthesis

An integrated photo-flow oxidative reaction (UV-FOR) platform approach is presented for the synthesis of phthalides. The current protocol is catalyst-free, and uses economical and abundant hydro-carbons and hydrocarbon derivatives such as benzoic acid, benzene, and xylene, as starting materials. The reaction is performed using oxygen as a green oxidant in a time- and labour-efficient manner. This integrated approach has been shown to be successful in making a UV-FOR platform suitable for the on-demand synthesis of phthalides and their further syntheses to 2-arylmethylbenzoic acids and arylogous Michael addition products under relatively mild conditions. The current protocol was further extended to the gram scale synthesis of an ischemic stroke-relevant active pharmaceutical ingredient (API), 3-N-butylphthalide (NBP), in a continuous flow process.

Catalytic Friedel-Crafts acylation: Magnetic nanopowder CuFe 2O4 as an efficient and magnetically separable catalyst

Catalytic regioselective Friedel-Crafts acylation of an array of anisoles/arenes with various acid chlorides using 5-20 mol % of magnetic nanopowder CuFe2O4 is reported. Unlike the conventional Friedel-Crafts reactions, which are catalyzed by moisture sensitive homogeneous catalysts/promoters, the nanopowder CuFe2O4 catalyst is moisture insensitive and the product/ketone-catalyst isolation is easily achieved using the magnetic properties of CuFe2O4.

Esters as acylating reagent in a Friedel-Crafts reaction: Indium tribromide catalyzed acylation of arenes using dimethylchlorosilane

(Chemical Equation Presented) The Friedel-Crafts acylation of arenes with esters by dimethylchlorosilane and 10 mol % of indium tribromide has been achieved. The key intermediate RCOOSi(Cl)Me2 is generated from alkoxy esters with the evolution of the corresponding alkanes. The scope of the alkoxy ester moiety was wide: tert-butyl, benzyl, allyl, and isopropyl esters were successful. In addition, we demonstrated the direct synthesis of the indanone intermediate 11 of salviasperanol from ester 10.

Insertion of arynes into carbon-halogen σ-bonds: Regioselective acylation of aromatic rings

Arynes were found to insert into carbon-halogen σ-bonds of various acid halides, enabling acyl and halogen moieties to be introduced simultaneously into adjacent positions of aromatic rings. The Royal Society of Chemistry.

Antimony(V) chloride-benzyltriethylammonium chloride complex as an efficient catalyst for friedel-crafts acylation reactions

A novel catalytic system, the complex of antimony(V) chloride (SbCl 5) and benzyltriethylammonium chloride (TEBA), C6H 5CH2NEt3(SbCl5)2Cl complex, is described for Friedel-Crafts acylation reactions of aromatics with acyl and sulfonyl chlorides. The catalyst has a number of useful characteristics, such as ready access, minimal toxicity, reusability, insensitivity to atmosphere and moisture, rapid acylation with high yield, and ease of operation.

Preparative syntheses of optically pure ortho-substituted benzhydrols by asymmetric reductions of the corresponding benzophenones

Lithium aluminium hydride previously treated with 2.5 equivalents of (S)-(+) or (R)-(-)-2-(2-iso-indolinyl)butan-1-ol 3 (readily available reagents) reduced the five ortho-substituted benzophenones 4-6, 8 and 10 into the corresponding optically active benzhydrols with nearly 100% enantiomeric excesses. Other examples of asymmetric reductions of prochiral benzophenones are given.

LIQUID-PHASE CATALYTIC OXIDATION OF 2,5-DIMETHYLDIPHENYLMETHANE AND ITS METHYL-, CHLORO-, AND NITRO-SUBSTITUTED DERIVATIVES

The oxidation of 2,5-dimethyldiphenylmethane and its methyl, chloro, and nitro derivatives with oxygen in acetic acid in the presence of cobalt-manganese-bromide catalyst to benzophenone-2,5-dicarboxylic acids takes place with the intermediate formation of either 2,5-dimethylbenzophenones or products from oxidation of the methyl groups.The ratio of the oxidation paths depends on the nature of the substituent, and the contribution from the path involving initial oxidation of the methylene fragment changes with the substituents in the order 4'-CH3>H>4'-Cl>2'-Cl>4'-NO2.