76311-89-2

Usage

Uses

Used in Organic Synthesis:
3-bromofuran-2(5H)-one is used as a building block for the synthesis of various bioactive molecules due to its unique structure and properties.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-bromofuran-2(5H)-one is used as a starting material for the preparation of more complex compounds, contributing to the development of new drugs and therapeutic agents.
Used in the Production of Pharmaceuticals:
3-bromofuran-2(5H)-one is utilized as an intermediate in the production of pharmaceuticals, agrochemicals, and other fine chemicals, playing a crucial role in the synthesis of natural products and bioactive compounds with specific properties.
Used as a Reagent in Chemical Reactions:
3-bromofuran-2(5H)-one is employed as a reagent in various chemical reactions, facilitating the synthesis of target compounds and contributing to the advancement of chemical research and development.

InChI:InChI=1/C4H3BrO2/c5-3-1-2-7-4(3)6/h1H,2H2

Upstream product

• 7218-52-2 4-hydroxy-2-butynoic acid 
• 90085-85-1 3,4-dibromo-2,5-dimethoxy-tetrahydro-furan-2-carboxylic acid methyl ester 
• 31555-05-2 methyl 4-hydroxy-2-butynoate 
• 117858-88-5 (3S,4S)-4-Bromo-4-hydroxytetrahydrofuran-2-one 
• 2434-03-9 4,5-dibromo-2-furoic acid 
• 10035-10-6 hydrogen bromide 
• 72167-53-4 3-bromo-2,5-dimethoxy-2,5-dihydro-furan 
• 91468-55-2 3,4-dibromo-2,5-dimethoxytetrahydrofuran 
• 64-17-5 ethanol 
• 497-23-4 2-buten-4-olide 
• 200807-25-6 2,3,4-tribromo-butyric acid 

Downstream Products

• 76311-82-5 2,6-Dioxo-1-phenyl-hexahydro-furo[3,4-b]pyrrole-3-carboxylic acid methyl ester 
• 910219-34-0 [(3-bromofuran-2-yl)oxy]triisopropylsilane 
• 1223157-54-7 (R)-3-bromo-5-((R)-hydroxy(phenyl)methyl)furan-2(5H)-one 
• 1223157-55-8 3-bromo-5-((R)-hydroxy(phenyl)methyl)furan-2(3H)-one 
• 1258849-46-5 3-(2-nitrophenyl)furan-2(5H)-one 
• 1402611-59-9 3-[(E)-2-phenylethenyl]-2,5-dihydrofuran-2-one 
• 143392-20-5 3-(2-methylphenyl)-2,5-dihydrofuran-2-one 
• 1402611-53-3 3-(4-ethoxyphenyl)-2,5-dihydrofuran-2-one 
• 1402611-52-2 3-(4-tert-butylphenyl)-2,5-dihydrofuran-2-one 
• 1402611-56-6 3-(3,5-difluorophenyl)-2,5-dihydrofuran-2-one 
• 1402611-55-5 3-(3,5-dimethylphenyl)-2,5-dihydrofuran-2-one 
• 57200-23-4 3-phenyl-2(5H)-furanone 
• 1426390-47-7 C₁₉H₂₅NO₆ 
• 143392-19-2 3-(m-tolyl)furan-2(5H)-one 

Relevant academic research and scientific papers

3-Bromo-2,5-dihydrofuran-2-one and 4-bromo-2,5-dihydrofuran-2-one

Although 3-bromo-2,5-dihydrofuran-2-one and 4-bromo-2,5-dihydrofuran-2-one were first reported in 1894, considerable ambiguity still exists about the correct structure assignment of the two compounds. The present article gives a brief overview on the varying assignments of constitution and describes a novel method for the formation of 3-bromo-2,5-dihydrofuran-2-one. A comparison is made of the experimental 13C NMR chemical shifts with values predicted by increment calculations and experimental 1/C-C coupling constants are given for both compounds. Secure structural assignments are now available for both isomers.

A Sequential Pd-AAA/Cross-Metathesis/Cope Rearrangement Strategy for the Stereoselective Synthesis of Chiral Butenolides

A practical and highly enantio- (up to 94:6 er) and diastereoselective (up to >20:1 dr) synthesis of I-butenolides bearing two adjacent stereogenic centers is reported featuring a sequential direct palladium-catalyzed asymmetric allylic alkylation/(E)-selective cross-metathesis/[3,3]-sigmatropic Cope rearrangement from readily available α-substituted (5H)-furan-2-ones.

A palladium-catalyzed asymmetric allylic alkylation approach to α-quaternary γ-butyrolactones

The Pd-catalyzed asymmetric allylic alkylation (Pd-AAA) of enol carbonates derived from γ-butyrolactones is reported, affording the corresponding enantioenriched α,α′-disubstituted γ-butyrolactones in both high yields and high enantioselectivities (up to 94% ee). This method was eventually applied to the synthesis of chiral spirocyclic compounds.

Controlling the Substitution Pattern of Hexasubstituted Naphthalenes by Aryne/Siloxyfuran Diels–Alder Additions: Regio- and Stereocontrolled Synthesis of Arizonin C1 Analogs

3,4-Dimethoxybenz-1-yne and 2-siloxylated furans without or with a bromine atom at C-3 undergo Diels–Alder reactions with orientational selectivity. Hydrolysis furnished a bromine-free or a bromine-containing naphthalene, respectively. Bromination of the former provided a regioisomer of the latter. Either of the two compounds was processed to give a variety of unnatural naphthoquinonopyrano-γ-lactones. This occurred by a succession of (1) Heck coupling, (2) asymmetric dihydroxylation, (3) oxa-Pictet–Spengler cyclization, and (4) oxidation. The fifteen monomeric naphthoquinonopyrano-γ-lactone structures that we prepared resemble the natural product (–)-arizonin C1 or its C-5 epimer. Accordingly, they represent hexasubstituted naphthalenes likewise. The sixteenth naphthoquinonopyrano-γ-lactone that we synthesized is a kind of dimer. Its moieties are bridged differently than those in naturally occurring naphthoquinonopyrano-γ-lactone dimers.

Isotope-labeled methyl ketofuran, intermediate and method for preparing same

The invention discloses isotopically labeled methyl furanone, an intermediate and a preparation method of isotopically labeled methyl furanone. The invention provides isotopically labeled methyl furanone 6. The invention further provides a preparation method of isotopically labeled methyl furanone 6, and the preparation method comprises the following steps: performing removal of a hydroxy protecting group and isomerization reaction on a compound 20 in the presence of an acid. The method provided by the invention comprises short reaction steps, labeling loci are stable, are labeled on a common D ring of a strigolactone type compound family and are successfully butted with ABC rings of strigolactone type compounds to obtain a variety of isotopically labeled strigolactone type compounds with different isotopic abundances which are more than 99% respectively, and the isotopically labeled methyl furanone is applicable to wide substances, is used as an internal source standard matter for GC-MS and LC-MS/MS analysis and has high detection sensitivity and good accuracy, thereby having broad market application prospects.

Synthesis of stable isotopically labelled 3-methylfuran-2(5H)-one and the corresponding strigolactones

Conventional synthetic procedures of strigolactones (SLs) involve the independent synthesis of ring ABC and ring D, followed by a coupling of the two fragments. Here we prepared three kinds of stable, isotopically labelled D-ring analogues productively using a facile protocol. Then, a coupling of the D-rings to ring ABC produced three isotope-labelled SL derivatives. Moreover, (+)-D3-2′-epi-1A and (-)-ent-D3-2′-epi-1A with high enantiomeric purity were obtained via chiral resolution. We developed a convenient method to synthesize three kinds of stable, isotopically labelled D-ring analogues for subsequent production of isotope-labelled strigolactones. With this simple and universal method, three labelled 5-deoxystrigols (D3-1, 13C-1 and D313C-1) were synthesized.

Palladium-catalyzed asymmetric allylic alkylation of cyclic dienol carbonates: Efficient route to enantioenriched γ-butenolides bearing an all-carbon α-quaternary stereogenic center

Alpha, beta, gamma: Allyl dienol carbonates (1) served as substrates for the title reaction to afford the furanones 2 in both high yields and high enantioselectivities. These furanones were eventually converted into valuable building blocks including γ-tertiary and γ-quaternary furanones (3) as well as β-quaternary butyrolactones (4). This method was used as a key step in the total synthesis of (-)-nephrosteranic acid and (-)-roccellaric acid. Copyright

A modular and scalable one-pot synthesis of polysubstituted furans

One four all: Allyl dienol carbonates can be readily converted into diversely substituted furans by a one-pot four-step sequence featuring a palladium-catalyzed decarboxylative allylic alkylation, a microwave-mediated Cope rearrangement, a nucleophilic addition, and a dehydration reaction (see scheme). The protocol is operationally simple, highly flexible, and provides di-, tri-, and tetrasubstituted furans starting from readily available materials. Copyright

Formal intramolecular (4 + 1)-cycloaddition of dialkoxycarbenes: Control of the stereoselectivity and a mechanistic portrait

The stereoselective synthesis of 5-5, 6-5, and 7-5 fused O-heterocyclic compounds is reported. The key reaction is a formal intramolecular (4 + 1)-cycloaddition involving a dialkoxycarbene and an electron-deficient diene where the stereoselectivity is dependent on the length of the tether. An analysis of the stereochemical outcome of this reaction sheds light on its complex mechanistic picture. High-level calculations were used to support the proposed mechanistic portrait.

A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds

The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.