309254-29-3

Basic information

• Product Name: 2-BROMOBENZYL-(3-METHOXYPHENYL)ETHER
• Synonyms: 2-BROMOBENZYL-(3-METHOXYPHENYL)ETHER
• CAS NO: 309254-29-3
• Molecular Formula: C₁₄H₁₃BrO₂
• Molecular Weight: 293.16
• Mol File: 309254-29-3.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-BROMOBENZYL-(3-METHOXYPHENYL)ETHER(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOBENZYL-(3-METHOXYPHENYL)ETHER(309254-29-3)
• EPA Substance Registry System: 2-BROMOBENZYL-(3-METHOXYPHENYL)ETHER(309254-29-3)

Safety Data

• Hazardous Substances Data: 309254-29-3(Hazardous Substances Data)

Upstream product

• 150-19-6 O-methylresorcine 
• 3433-80-5 1-Bromo-2-bromomethyl-benzene 

Downstream Products

• 1068441-50-8 1-tert-butoxy-2-((3-methoxyphenoxy)methyl)benzene 
• 1068441-48-4 1-tert-butoxy-3-((3-methoxyphenoxy)methyl)benzene 
• 1143-62-0 3-Methoxy-6H-dibenzopyran-6-one 
• 21144-16-1 3-benzyloxyanisole 
• 185613-58-5 3-methoxy-6H-benzo[c]chromene 

Relevant articles and documents

Direct transition-metal-free intramolecular arylation of phenols

(Chemical Equation Presented) Direct transition-metal-free, base-mediated intramolecular arylation of phenols with aryl halides has been developed. In the presence of 2.5 equiv of t-BuOK in dioxane at 140 °C, the intramolecular cyclization of 3-(2-halobenzyloxy)phenols affords 6H-benzo[c]chromenes in high yields. This reaction proceeds by an initial formation of a benzyne intermediate followed by an aromatic sp2 C-H functionalization (a formal C-H activation) to form the carbon-carbon bond.

Bu3SnH mediated oxidative radical cyclisations: Synthesis of 6H-benzo[c]chromen-6-ones

Attempts to synthesise 6H-benzo[c]chromen-6-ones by Bu3SnH mediated cyclisation of o-(benzoyl)aryl radicals failed because of the preferred trans conformation of the ester. This problem was overcome by using cyclisation of o-(benzyloxy)aryl and o-[(aryloxy)methyl]aryl radicals to yield 6H-benzo[c]chromenes followed by oxidation to the 6H-benzo[c]chromen-6-ones. 3-Methoxy-6H-benzo[c]chromen-6-one 1, one of the main biologically active constituents of shilajit, a herbal medicine used in countries surrounding the Himalayan mountains, was synthesised using Bu3SnH mediated cyclisation of 1-benzyloxy-2,4-dibromo-5-methoxybenzene 31 to yield 3-methoxy-6H-benzo[c]chromene 25 followed by PCC oxidation of the 6-position. In order to avoid the problems of rearrangement, the aryl radical cyclisation must be designed such that whichever way the spirodienyl intermediate rearranges, the same product is obtained. For instance, the Bu3SnH mediated cyclisation of 1-iodo- and 1-bromo-2-(3-methoxy-phenyloxymethyl)benzenes 22 and 23 respectively gave both the isomers, 1-methoxy-6H-benzo[c]chromenes 24 and 3-methoxy-6H-benzo[c]chromenes 25 via rearrangement of the intermediate spirodienyl radical. The synthesised 6H-benzo[c]chromenes were oxidised in high yield to the corresponding 6H-benzo[c]chromen-6-ones. The mechanism of the 'oxidative' Bu3SnH mediated cyclisation is discussed.