64169-34-2

Usage

Uses

Used in Agrochemical Industry:
5-Bromophthalide is used as a synthetic intermediate for the development of various agrochemical products, contributing to the enhancement of crop protection and yield.
Used in Pharmaceutical Industry:
5-Bromophthalide serves as a key intermediate in the synthesis of pharmaceutical compounds, including the antidepressant drug citalopram, playing a crucial role in the development of medications for mental health.
Used in Dye Industry:
5-Bromophthalide is utilized as a synthetic intermediate in the production of dyes, enabling the creation of a diverse range of colorants for various applications, such as textiles, plastics, and printing inks.
Used in Chemical Synthesis:
5-Bromophthalide is a useful synthetic intermediate in the chemical industry, facilitating the production of various compounds and materials with specific properties and applications.

InChI:InChI=1/C8H5BrO2/c9-6-1-2-7-5(3-6)4-11-8(7)10/h1-3H,4H2

Upstream product

• 65399-05-5 5-amino-3H-isobenzofuran-1-one 
• 68837-59-2 4-bromo-2-methylbenzoic acid 
• 888030-82-8 (5-bromo-3H-isobenzofuran-1-ylidene)-isopropyl-amine 
• 1467-79-4 NCNMe₂ 
• 171011-37-3 4-bromo-2-(hydroxymethyl)benzyl alcohol 
• 220513-49-5 5-bromo-1,3-dihydroisobenzofuran 
• 87-41-2 2-benzofuran-1(3H)-one 
• 85-44-9 phthalic anhydride 
• 6968-28-1 4-bromophthalic acid 
• 6941-75-9 5-Bromoisoindoline-1,3-dione 
• 6245-57-4 4-methoxy-2-methylbenzoic acid 
• 50-00-0 formaldehyd 
• 127580-92-1 (4-bromophenyl)(morpholino)methanone 
• 69189-19-1 4-bromo-1,2-bis-bromomethyl-benzene 

Downstream Products

• 171011-37-3 4-bromo-2-(hydroxymethyl)benzyl alcohol 
• 670256-21-0 4-bromo-2-(hydroxymethyl)benzoic acid 
• 888030-76-0 4-bromo-2-hydroxymethyl-N-propyl-benzamide 
• 888030-77-1 4-bromo-2-hydroxymethyl-N-(4-methoxy-benzyl)-benzamide 
• 864866-47-7 5-bromo-2-(propan-2-yl)-2,3-dihydro-1H-isoindol-1-one 
• 888030-75-9 N-isopropyl-4-bromo-2-hydroxymethylbenzamide 
• 888030-78-2 4-bromo-N-tert-butyl-2-hydroxymethyl-benzamide 
• 888030-79-3 4-bromo-2-(hydroxymethyl)-N-methylbenzamide 
• 64169-66-0 5-bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran 
• 64169-65-9 4-bromo-(2-hydroxymethyl)-phenyl-(4'-fluorophenyl)methanol 
• 488148-10-3 4-(4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzobromide 
• 862081-37-6 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isobenzofuran-1(3H)-one 
• 862081-38-7 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isobenzofuran-1(3H)-one 
• 64169-64-8 4-bromo-4'-fluoro-2-(hydroxymethyl)benzophenone 

Relevant academic research and scientific papers

Visible Light-Promoted Magnesium, Iron, and Nickel Catalysis Enabling C(sp3)-H Lactonization of 2-Alkylbenzoic Acids

A mild and practical C(sp3)-H lactonization protocol has been achieved by merging photocatalysis and magnesium (iron, nickel) catalysis. A diverse range of 2-alkylbenzoic acids with a variety of substitution patterns could be transformed into the corresponding phthalide products. Based on the mechanistic experimentation and reported prior studies, a possible mechanism for the benzylic oxidative lactonization reaction was proposed with the hypothetic photoactive ternary complex formed between the 2-alkylbenzoic acid substrate, magnesium ion, and bromate anion.

Squaramide-catalyzed asymmetric intramolecular oxa-michael reaction of α,β-unsaturated carbonyls containing benzyl alcohol: Construction of chiral 1-substituted phthalans

Organocatalytic enantioselective intramolecular oxa-Michael reactions of benzyl alcohol bearing α,β-unsaturated carbonyls as Michael acceptors are presented herein. Using cinchona squaramide-based organocatalyst, enones as well as α,βunsaturated esters containing benzyl alcohol provided their corresponding 1,3-dihydroisobenzofuranyl-1-methylene ketones and 1,3-dihydroisobenzofuranyl-1-methylene esters in excellent yields with high enantioselectivities. In addition, enantioenriched 1,3-dihydroisobenzofuranyl-1-methylene ketone could be obtained from the Wittig/oxa-Michael reaction cascade of 1,3-dihydro-2-benzofuran-1-ol.

Enantioselective synthesis of 3-aryl-phthalides through a nickel-catalyzed stereoconvergent cross-coupling reaction

A nickel-catalyzed asymmetric Suzuki-Miyaura cross-coupling of racemic 3-bromo-phthalides and arylboronic acids was realized for the synthesis of diverse chiral 3-aryl-phthalides in moderate to excellent reaction yields. The reaction proceeded in a stereoconvergent manner and high enantioselectivities were observed for most examined examples. A number of functional groups like aldehyde, ester and bromide were well tolerated. Heteroaromatic boronic acids were also competent coupling partners in this reaction.

Organocatalytic enantioselective synthesis of phthalans via Wittig/oxa-Michael cascade reaction

An enantioselective synthetic method for 1-substituted phthalans has been developed. The organocatalytic reaction between 1,3-dihydro-2-benzofuran-1-ols and Wittig reagents using cinchona squaramide-based organocatalyst proceeded with sequential Wittig reaction followed by an enantioselective intramolecular oxa-Michael reaction, yielding enantioenriched phthalans with moderate to good enantioselectivities.

Design, synthesis and biological evaluation of novel thiohydantoin derivatives as potent androgen receptor antagonists for the treatment of prostate cancer

Prostate cancer (PC) is the most common malignancy in men worldwide. Here, two series of novel thiohydantoin derivatives of enzalutamide as potent androgen receptor (AR) antagonists were designed and synthesized. Among them, compound 31c was identified as an AR antagonist which is 2.3–fold more potent than enzalutamide. Molecular docking studies were performed to explain the improved potency of 31c at AR. In cell proliferation assays, 31c exhibited similar anti-proliferative activities with enzalutamide against hormone sensitive LNCaP cells and AR-overexpressing LNCaP/AR cells. These data indicate that 31c can be a good lead compound for further structure optimization for the treatment of prostate cancer.

N-Heterocyclic Carbene Catalyzed Ester Synthesis from Organic Halides through Incorporation of Oxygen Atoms from Air

Oxygenation reactions with molecular oxygen (O2) as the oxygen source provides a green and straightforward strategy for the construction of O-containing compounds. Demonstrated here is a novel N-heterocyclic carbene (NHC) catalyzed oxidative transformation of simple and readily available organic halides into valuable esters through the incorporation of O-atoms from O2. Mechanistic studies prove that the deoxy Breslow intermediate generated in situ is oxidized to a Breslow intermediate for further transformation by this oxidative protocol. This method broadens the field of NHC catalysis and promotes oxygenation reactions with O2.

Chiral Bicyclic Imidazole-Catalyzed Acylative Dynamic Kinetic Resolution for the Synthesis of Chiral Phthalidyl Esters

Utilizing a chiral bicyclic imidazole organocatalyst and adopting a continuous injection process, an alternative route has been developed for the efficient synthesis of chiral phthalidyl ester prodrugs via dynamic kinetic resolution of 3-hydroxyphthalides through enantioselective acylation (up to 99 % ee). The computational studies suggest a general base catalytic mechanism differing from the widely accepted nucleophilic catalytic mechanism. The structure analysis of the key transition states shows that the CH-π interactions and not the previously considered cation/π-π interactions between the catalyst and substrate is the dominant factor giving rise to the observed stereocontrol.

Synthesis of 3-Unsubstituted Phthalides from Aryl Amides and Paraformaldehyde via Ruthenium(II)-Catalyzed C–H Activation

A straightforward and convenient route has been developed for the synthesis of 3-unsubstituted phthalide derivatives from aryl amides and paraformaldehyde by ruthenium(II)-catalyzed C–H activation. The reaction proceeds through tandem ortho-hydroxymethylation of aryl amide and subsequent intramolecular lactonization.

Platinum-on-Carbon-Catalyzed Aqueous Oxidative Lactonization of Diols by Using Molecular Oxygen

A lactonization of various diols catalyzed by platinum on carbon (Pt/C) in water under an atmosphere of molecular oxygen was developed. Derivatives of 1,4- 1,5- and 1,6-diols were transformed into the corresponding five-, six-, and seven-membered lactones by the present oxidative lactonization method.

Method for synthesizing roxadustat intermediate

The invention belongs to the technical field of chemical preparation, and discloses a method for synthesizing a roxadustat intermediate. The method comprises the following steps: mixing 4-bromo-2-methylbenzoic acid and a solvent to obtain a mixture 1, adding N-bromosuccinimide and an initiator into the mixture 1, performing uniform mixing to obtain a mixture 2, and performing a reaction to obtainthe roxadustat intermediate 5-bromophthalide. The method provided by the invention has the following advantages: the method for synthesizing the roxadustat intermediate provided by the invention adopts the 4-bromo-2-methylbenzoic acid as the reaction raw material, the raw material is simple and easy to obtain, the costs are low, the reaction is easy to control, and the final product 5-bromophthalide has a yield of 96.5% or more and purity of 98.5% or more.