1326704-95-3

Basic information

• Product Name: 7-chloro-2,3-dihydro-5-methoxy-2-phenylbenzofuran
• Synonyms: 7-chloro-2,3-dihydro-5-methoxy-2-phenylbenzofuran
• CAS NO: 1326704-95-3
• Molecular Weight: 260.72
• Mol File: 1326704-95-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 7-chloro-2,3-dihydro-5-methoxy-2-phenylbenzofuran(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-2,3-dihydro-5-methoxy-2-phenylbenzofuran(1326704-95-3)
• EPA Substance Registry System: 7-chloro-2,3-dihydro-5-methoxy-2-phenylbenzofuran(1326704-95-3)

Safety Data

• Hazardous Substances Data: 1326704-95-3(Hazardous Substances Data)

Upstream product

• 18113-03-6 2-chloro-4-methoxyphenol 
• 100-42-5 styrene 
• 57197-15-6 2-chloro-4,4-dimethoxycyclohexa-2,5-dien-1-one 

Relevant articles and documents

Br?nsted acid-controlled [3 + 2] coupling reaction of quinone monoacetals with alkene nucleophiles: A catalytic system of perfluorinated acids and hydrogen bond donor for the construction of benzofurans

We have developed an efficient Br?nsted acid-controlled strategy for the [3 + 2] coupling reaction of quinone monoacetals (QMAs) with nucleophilic alkenes, which is triggered by the particular use of a specific acid promoter, perfluorinated acid, and a solvent, fluoroalcohol. This new coupling reaction smoothly proceeded with high regiospecificity in regard with QMAs for introducing π-nucleophiles to only the carbon α to the carbonyl group, thereby providing diverse dihydrobenzofurans and derivatives with high yields, up to quantitative, under mild conditions in short reaction times. The choice of Br?nsted acid enabled us to avoid hydrolysis of the QMAs, which gives quinones, and the formation of discrete cationic species from the QMAs. Notably, further investigations in this study with regard to the acid have led to the findings that the originally stoichiometrically used acid could be reduced to a catalytic amount of 5 mol % loading or less and that the stoichiometry of the alkenes could be significantly improved down to only 1.2 equiv. The facts that only a minimal loading (5 mol %) of perfluoroterephthalic acid is required, readily available substrates can be used, and the regioselectivity can be controlled by the acid used make this coupling reaction very fascinating from a practical viewpoint.

[3 + 2] coupling of quinone monoacetals by combined acid-hydrogen bond donor

The expeditious and efficient [3 + 2] coupling approach of quinone monoacetals 1 with alkene nucleophiles 2 by the action of an activated Bronsted acid in the presence of a hydrogen bond donor perfluorinated alcohol has been achieved. With the optimized combined acid, the reaction could proceed under mild conditions by only mixing the two reactants to afford the cycloadducts 3 in a short time (within 10 min) with good to quantitative yields.