26965-67-3

Upstream product

• 108-86-1 bromobenzene 
• 635-93-8 5-chlorosalicyclaldehyde 
• 106-48-9 4-chloro-phenol 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 65141-85-7 (2S,4R)-6-Chloro-4-phenyl-4H-benzo[1,3]dioxine-2-carboxylic acid 
• 65141-85-7 (2R,4R)-6-Chloro-4-phenyl-4H-benzo[1,3]dioxine-2-carboxylic acid 
• 67059-67-0 6-chloro-4-phenyl-[4H]-1,3-benzodioxin-2-carboxylic acid 
• 1094415-57-2 ethyl 6-chloro-2-methyl-4-phenyl-4H-chromene-3-carboxylate 
• 1186642-10-3 4-chloro-2-(1-phenylbut-3-enyl)phenol 
• 1245449-32-4 (6-chloro-2-(methylthio)-4-phenyl-4H-chromen-3-yl)(phenyl)methanone 

Relevant academic research and scientific papers

A simple synthesis of benzofurans by acid-catalyzed domino reaction of salicyl alcohols with N-tosylfurfurylamine

A simple route to polysubstituted benzofurans based on the domino reaction of commercial or easily available salicyl alcohols with N-protected furfurylamine has been designed and developed. The reaction was found to proceed with reasonable yields under heating of substrates in acetic acid in the presence of catalytic amount of conc. HCl when tosyl was used as protecting group.

Catalytic Asymmetric Three-component Hydroacyloxylation/ 1,4-Conjugate Addition of Ynamides

A highly enantioselective three-component hydroacyloxylation/1,4-conjugate addition of ortho-hydroxybenzyl alcohols, ynamides and carboxylic acids was developed under mild reaction conditions in the presence of a chiral N,N′-dioxide/Sc(OTf)3 complex, which went through in situ generated ortho-quinone methides with α-acyloxyenamides, delivering a range of corresponding chiral α-acyloxyenamides derivatives containing gem(1,1)-diaryl skeletons in moderate to good yields with excellent ee values. The scale-up experiment and further derivation showed the practicality of this catalytic system. In addition, a possible catalytic cycle and transition state model was proposed to elucidate the origin of the stereoselectivity based on X-ray crystal structure of the α-acyloxyenamide intermediate and product.

[4 + 2]-Cycloaddition and 1,4-Addition of ortho-Quinone Methides by a Chiral Crotyl Silane

Anhydrous FeCl3 in the presence of 2,6-lutidine promotes the substrate-controlled enantioselective [4 + 2]-cycloaddition and crotylation reaction between an enantioenriched (S,E)-crotyl silane and in situ generated ortho-quinone methides (oQMs)

Organocatalytic Asymmetric Domino Michael/Acyl Transfer Reaction Between α-Nitroketones and in situ-Generated ortho-Quinone Methides: Route to 2-(1-Arylethyl)phenols

An organocatalytic asymmetric domino Michael/acyl transfer reaction between α-nitroketones and o-quinone methides is disclosed. o-Quinone methides are generated in situ from 2-sulfonylmethylphenols in basic medium. With 10 mol% of bifunctional squaramide catalyst, high yields and excellent enantioselectivities are achieved for a variety of O-acyl 2-(1-arylethyl)phenols under mild reaction condition. (Figure presented.).

Multicomponent Condensation Reactions via ortho-Quinone Methides

Iron(III) salts promote the condensation of aldehydes or acetals with electron-rich phenols to generate ortho-quinone methides that undergo Diels - Alder condensations with alkenes. The reaction sequence occurs in a single vessel to afford benzopyrans in up to 95% yield. The reaction was discovered while investigating a two-component strategy using 2-(hydroxy(phenyl)methyl)phenols to access the desired ortho-quinone methide in a Diels - Alder condensation. The two-component condensation also afforded the corresponding benzopyran products in yields up to 97%. Taken together, the two- and three-component strategies using ortho-quinone methide intermediates provide efficient access to benzopyrans in good yields and selectivities.

Bifunctional Amine-Squaramide Catalyzed Friedel–Crafts Alkylation Based on ortho-Quinone Methides in Oil-Water Phases: Enantioselective Synthesis of Triarylmethanes

An efficient enantioselective Friedel–Crafts alkylation reaction of electron-rich β-naphthol with in situ generated ortho-quinone methides catalyzed by chiral bifunctional amine-squaramide catalysts has been developed. The chiral triarylmethane derivative

Organocatalytic Phosphonylation of in Situ Formed o-Quinone Methides

A new class of Br?nsted acid catalysts based on N-heterocyclic phosphorodiamidic acids (NHPAs) has been developed. The NHPA catalyst promotes phospha-Michael addition reaction of trialkylphosphites to in situ generated ortho-quinone methides (o-QMs) for t

One step synthesis of 2-alkenylchromanes via inverse electron-demand Hetero-Diels–Alder reaction of o-quinone methide with unactivated dienes

The synthetically important 2-alkenylchromane derivatives were constructed in good yields under metal-free condition via inverse electron demand Hetero-Diels–Alder reaction of o-quinone methides with unactivated dienes. This strategy features mild conditi

One-pot synthesis of 3,4-disubstituted coumarins under catalysis of Mn 3O4 nanoparticles

The one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles was developed. A series of 3,4-disubstituted coumarin derivatives were obtained in good yields. A new method for the one-pot synthesis of 3,4-disubstituted coumarins from substituted 2-(hydroxymethyl)phenols with β-keto esters catalyzed by Mn 3O4 nanoparticles has been developed. A series of 3,4-disubstituted coumarin derivatives were synthesized from substituted 2-(hydroxymethyl)phenols and β-keto esters in good yields. Copyright

One-pot synthesis of polyfunctionalized 4H-chromenes and dihydrocoumarins based on copper(II) bromide-catalyzed C-C coupling of benzylic alcohols with ketene dithioacetals

The synthesis of polyfunctionalized 4Hchromenes 3 and dihydrocoumarins 4 has been developed from the same substrates. Catalyzed by copper(II) bromide (0.3 equiv.), the reactions of the easily available ketene dithioacetals 1 with 2-(hydroxymethyl)phenols 2 lead to 4/7-chromenes 3 in high to excellent yields in dichloromethane solvent, whereas, 3,4-trans-disubstituted dihydrocoumarins 4 are obtained in high yields with high diastereoselectivities by prolonging the reaction time or changing the solvent from dichloromethane to acetonitrile.