56660-59-4

Usage

Uses

Used in Organic Synthesis:
2,3-dibromotetrahydro-2H-pyran is used as a versatile building block for the preparation of various organic compounds, contributing to the synthesis of a diverse array of chemical products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 2,3-dibromotetrahydro-2H-pyran is utilized as a reagent in the synthesis of various pharmaceuticals, aiding in the development of new drugs and medicinal compounds.
Used in Agrochemical Synthesis:
2,3-dibromotetrahydro-2H-pyran also serves as a reagent in the synthesis of agrochemicals, playing a role in the creation of products used in agriculture to enhance crop protection and yield.
Used in the Production of Fine Chemicals:
2,3-dibroMotetrahydro-2H-pyran is employed in the synthesis of fine chemicals, which are high-purity chemicals used in various applications, including research, diagnostics, and specialty manufacturing.
Used as an Intermediate in Chemical Production:
2,3-dibromotetrahydro-2H-pyran is considered a useful intermediate in the production of a wide range of chemical products, highlighting its importance in the field of organic chemistry and the broader chemical industry.

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 56-23-5 tetrachloromethane 
• 128-08-5 N-Bromosuccinimide 
• 26274-19-1 5-bromo-3,4-dihydro-2H-pyran 
• 94-36-0 dibenzoyl peroxide 

Downstream Products

• 5324-21-0 3-bromo-2-methoxy-tetrahydropyran 
• 39150-42-0 3-Brom-2-aethoxytetrahydropyran 
• 81991-71-1 3-bromo-2-phenyl-tetrahydro-pyran 
• 6559-34-8 6-methoxy-3,6-dihydro-2H-pyran 
• 156051-16-0 (+/-)-3-bromo-2-methyloxane 
• 31518-14-6 3,4-dihydro-2H-pyran-6-carboxylic acid 
• 31518-13-5 3,4-dihydro-2H-pyran-6-carbonitrile 
• 31502-21-3 (E)-oct-4-en-1-ol 
• 105499-32-9 (S)-(-)-Tetrahydropyran-2-carboxylic Acid 
• 1051940-71-6 3-Bromo-tetrahydro-pyran-2-carbonitrile 
• 58223-46-4 7-methylnonanal 
• 13047-01-3 3-bromotetrahydro-2H-pyran 

Relevant academic research and scientific papers

Iridium-catalyzed enantioselective hydrogenation of unsaturated heterocyclic acids

Spiral binding: A highly enantioselective hydrogenation of unsaturated heterocyclic acids has been developed by using chiral iridium/spirophosphino oxazoline catalysts (see scheme; BArF-=tetrakis[3,5- bis(trifluoromethyl)phenyl]borate, Boc=tert-butoxycarbonyl). This reaction provided an efficient method for the preparation of optically active heterocyclic acids with excellent enantioselectivities. Copyright

"Furan endwise peeling" of celluloses: Mechanistic studies and application perspectives of a novel reaction

The mechanism of a novel reaction type, the "furan endwise peeling" reaction, has been studied. Making extensive use of experiments on model compounds, the structural prerequisites to the reaction were found to be a 2-hydroxpyran β-glycosidically linked t

SYNTHESIS OF THE RACEMIC PROPIONATE OF 8-METHYL-2-DECANOL, THE SEX HORMONE OF THE SEVERAL LEAF-EATING BUGS Diabrotica (CHRYSOMELIDAE)

A new method has been developed for the synthesis of sex hormone of Diabrotica leaf-eating bugs, namely, the racemic propionate of 8-methyl-2-decanol, from 7-methyl-1-nonanol, which, in turn, was obtained by two methods using the Grignard reaction from furfural and from 2,3-dibromotetrahydropyran.

Enantioselective Total Synthesis of (-)-Monic Acid C via Carbosulfenylation of Dihydropyran

A stereoselective synthesis of (-)-monic acid C (5) was accomplished in a linear sequence of 22 steps beginning from dihydropyran and with (-)-1-borneol as a chiral auxiliary. 2-(1-Bornyloxy)pyrans 10 and 11 were converted via trans epoxides 12 and 13 to hydroxy selenides 16 and 17.Selenide 16 was transformed to vinyl ether 20, which underwent Claisen rearrangement to 22.The latter, after oxidation to carboxylic acid 24, was treated with stannic chloride to give the γ-lactone 26.A parallel sequence from 17 brought this selenide, via 29 and its Claisen rearrangement product 31, into convergence with 26.Carbosulfenylation of 26 in the presence of 2-(trimethylsiloxy)propene was accompanied by elimination and led to 33 and its trans isomer 34.Cis hydroxylation of 33, protection of the resulting diol, and Horner-Emmons condensation of 41 with tert-butyl dimethyl-phosphonoacetate gave 43.Attachment of the second side chain of 5 was effected by means of a Julia olefination of 46 with sulfone 65, prepared from ethyl (2S,3S)-3-hydroxy-2-methylbutanoate.The resulting substituted tetrahydropyran 68, after removal of the three protecting groups, yielded 5.

THE STERIC COURSE OF THE REACTIONS OF 2,3-DIHALOTETRAHYDROPYRANS WITH GRIGNARD REAGENTS

The steric course of some reactions of 2,3-dihalotetrahydropyrans with sodium methoxide and with methyl- and phenyl-magnesium bromides has been reinvestigated.Whereas the methanolysis of the cis- and trans-dichlorides occurs with practically complete inversion, it has been confirmed that their reactions, as well as those of dibromides, with methylmagnesium bromide are non-stereospecific, yielding mixtures of trans- and cis-3-halo-2-methyl-tetrahydropyrans in ratios that are independent of the configurations of the starting dihalides.It has been further established that grignard reagents cause equlibration of cis- and trans-dihalide mixtures in a reaction that is much faster than the Grignard coupling step.

One-Pot Preparation of α-Cyanovinyl Ethers (2-Alkoxy-2-alkenenitriles) from Vinyl Ethers: Elaboration to 3-Alkoxy-2-oxo-3-alkenenitriles and Aluminium Chloride-Catalyzed Cycloadditions to Cyclopentadiene

A variety of α-cyanovinyl ethers have been prepared by 3 different routes and elaborated to 3-alkoxy-2-oxo-3-alkenenitriles.The latter, in the presence of cyclopentadiene and aluminium chloride, give novel bridged 7-membered cycloadducts with loss of hydrogen cyanide.

β-Halogeno Ether Synthesis of Olefinic Alcohols: Stereochemistry and Conformation of 2-Substituted 3-Halogenotetrahydro-pyran and furan Precursors

Ring-scission of cis- or trans-2-alkyl- (or aryl-) 3-chlorotetrahydropyrans proceeds regioselectively and highly stereoselectively to give (E)-alk-4-en-1-ols, but in the parallel tetrahydrofuran series (Z)-/(E)-mixtures, dependent on percursor geometry, are formed.In this paper the stereochemistry and conformation of the tetrahydro-pyran and - furan precursors are considered.The cis/trans-composition of 2,3-dihalogenotetrahydro-pyrans and-furans made by various routes is reported.Reaction with Grignard reagents gives separable cis-/trans-mixtures the stereoisomeric composition of which, in the cases examined, does not depend on the stereoisomeric composition of the dihalide, but does vary with the halogen and the composition of the Grignard or dialkylmagnesium; possible reasons are discussed.The stereochemistry and conformation of the 2-alkyl- (or aryl-)3-chlorotetrahydropyrans is analysed by n.m.r. methods (J2a,3acis ca. 1.5 Hz; J2a,3atrans ca. 9.8 Hz) but assignments for the two tetrahydrofuran series with J2,3 2.6-3.6 and 4.3-5.9 are made uncertain by pseudorotation.The stereochemical identity of the two series is rigorously proved by isolation of cis- and trans-2-allyl-3-chlorotetrahydrofuran.On the one hand the former is hydrogenated to the cis-2-propyl compound, correlated with other members of the alkyl series, but on the other it is oxidised and the acid is converted into the cis-p-bromophenyl ester.The stereochemistry and conformation of the latter is rigorously demonstrated by an X-ray structure.The stereochemistries and conformations of the 2-deuterio- and 2-methoxy-3-chlorotetrahydropyrans are discussed, and consideration is then extended to the 2-alkyl-3-chloro-2-methyltetrahydro-pyran and -furan series.

PREPARATION OF 3-BROMO-2-ETHOXY-5,6-DIHYDRO-2H-PYRAN

The isolation and characterisation of compounds 5 and 6 are described.According to NMR spectra, the preferred conformations of these substances are 5b and 6b, respectively.Dehydrobromination of 6 using sodium hydride in 1,2-dimethoxyethane provided 3-bromo-2-ethoxy-5,6-dihydro-2H-pyran, 2.Reaction of 3α,4β-dibromo-2β-ethoxytetrahydropyran, 1b, with sodamide in the same solvent also afforded 2.