29568-65-8

Usage

Molecular structure

2-(1-bromoethyl)-2-phenyl-1,3-dioxolane consists of a dioxolane ring with a bromoethyl and a phenyl group attached to it.

Usage in organic synthesis

Commonly used as a reagent for creating new chemical compounds.

Application in pharmaceuticals and agrochemicals

Serves as a starting material for the preparation of various pharmaceuticals and agrochemicals.

Potential solvent and polymer stabilizer

Has potential uses as a solvent and a stabilizer for polymers.

Importance in synthesis of bioactive molecules and materials

Due to its unique structure and versatile reactivity, it is an important intermediate in the synthesis of various bioactive molecules and materials.

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 4359-49-3 2-ethyl-2-phenyl-1,3-dioxolane 
• 107-21-1 ethylene glycol 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 

Downstream Products

• 80550-06-7 2-hydroxyethyl-2-phenylpropanoate 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 29568-62-5 2-ethynyl-2-phenyl-1,3-dioxolane 
• 29568-67-0 2-(1,2-dibromo-ethyl)-2-phenyl-[1,3]dioxolane 
• 33662-99-6 2-chloroethyl 2-phenylpropionate 
• 93-55-0 1-phenyl-propan-1-one 
• 29568-66-9 2-phenyl-2-vinyl-[1,3]dioxolane 
• 143164-78-7 5-methyl-6-phenyl-2,3-dihydro-1,4-dioxine 
• 91306-39-7 2-Phenyl-2-(1-phenylselanyl-ethyl)-[1,3]dioxolane 
• 4359-49-3 2-ethyl-2-phenyl-1,3-dioxolane 
• 2412-73-9 benzoic acid cyclohexyl ester 
• 768-03-6 Phenyl vinyl ketone 
• 91306-44-4 2-phenyl-2-(1-phenyltelluro)ethyl-1,3-dioxolane 

Relevant academic research and scientific papers

Practical synthesis of functionalized terminal alkynes, 3,3,3-triethoxypropyne and ketal protected prop-2-ynones

Practical and economical synthesis of synthetically valuable 3,3,3-triethoxypropyne, ketal protected phenyl and methyl substituents prop-2-ynones is described. Bromination and subsequent 18-crown-6 catalyzed elimination of triethylorthoacrylate and ketal

Novel Preparation of α,β-Unsaturated Aldehydes. Benzeneselenolate Promotes Elimination of HBr from α-Bromoacetals

Acetalization, α-bromination, nucleophilic phenylselenenylation, oxidative elimination/hydrolysis was investigated as a novel protocol for the α,β-dehydrogenation of aldehydes. Treatment of acetals with bromine in methylene chloride afforded the corresponding α-bromoacetals in 80-90% yields. Nucleophilic phenylselenenylation was then conveniently effected by treatment with benzenese-lenolate generated in situ in dimethyl sulfoxide from diphenyl diselenide, hydrazine and potassium carbonate. Unbranched α-bromoacetals cleanly afforded substitution products whereas β- and γ-branched ones gave substantial amounts of α,β-unsaturated acetals via formal loss of hydrogen bromide. Oxidative elimination/hydrolysis of these mixtures afforded α,β-unsaturated aldehydes in 50-80% overall yields. In the case of tertiary α-bromoacetals, treatment with benzeneselenolate afforded only dehydrobromination products as mixtures of isomers. The presence of at least a catalytic amount of the organoselenium reagent was found to be crucial for olefin formation. A SET-mechanism, involving benzeneselenolate-induced electron transfer to the halide, loss of bromide ion, and hydrogen atom or proton/electron was proposed for the benzenselenolate-promoted elimination reaction. Experiments designed to trap carbon-centered radicals in intramolecular cyclization or ring-opening reactions failed to provide any evidence for free-radical intermediates.

Application of Oxidative Aryl Migration in Organo-selenium and -tellurium Compounds to the Synthesis of 2-Arylpropanoic Acids

The ethylene acetals of aryl α-phenylseleno- and α-phenyltelluro-ethyl ketones i, Ph, Br) and 5-bromo-6-methoxy-2-naphthyl> have been prepared in 12-83percent yields by treating the corresponding α-bromo compounds with diphenyl diselenide-sodium or diphenyl ditelluride-sodium, respectively, in tetrahydrofuran-dimethylformamide under reflux for 6-10 h, during which the bromine is substituted by the PhSe or PhTe group.This substitution is not observed when the (PhM)2-NaBH4-EtOH (M=Se, Te) system which is known as a source of PhM- anion is used.Oxidation of the acetals thus formed with an excess of meta-chloroperbenzoic acid at 20-25 deg C for 1 h affords hydroxy-ethyl 2-arylpropanoates in 56-86percent yields via aryl group migration which are hydrolysed to 2-arylpropanoic acids, some of which are pharmaceutically important compounds.Overall isolated yields of 2-arylpropanoic acids are around 30-42percent based on the starting propiophenones over 5 steps.

ONE-STEP SYNTHESIS OF SUBSTITUTED 2-ARYL-2-BROMOALKYL-1,3-DIOXOLANES

Substituted phenones II reacted with ethylene glycol and pyridinium perbromide, phenyltrimethylammonium tribromide, or dioxane dibromide to give the corresponding α-bromoacetals I.The highest yields are obtained with dioxane dibromide, and a route is suggested in which the agent is generated in situ.The mass spectra of the compounds I are interpreted.

New Preparative Method for 2-Arylpropanoic Acids by Oxidative Aryl Migration in Aryl α-Seleno- and Aryl α-Telluro-ethyl Ketones

Oxidation with m-chloroperbenzoic acid of the ethylene acetals of aryl α-phenylseleno- or aryl α-phenyltelluro-ethyl ketones prepared by treating the corresponding α-bromo compounds with diphenyl diselenide-sodium or diphenyl ditelluride-sodium, respectively, affords hydroxyethyl 2-arylpropanoates in moderate to good yields via aryl group migration.