28314-83-2

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromo-2,4-difluoro-benzoic acid is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity enable the development of novel drug candidates with improved therapeutic properties and efficacy.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Bromo-2,4-difluoro-benzoic acid serves as a crucial component in the production of pesticides and other agrochemicals. Its incorporation into these compounds enhances their effectiveness in controlling pests and diseases, thereby contributing to increased crop yields and food security.
Used in Materials Science:
5-Bromo-2,4-difluoro-benzoic acid is employed as a building block in the synthesis of advanced materials with specific properties. Its unique structure allows for the creation of materials with tailored characteristics, such as improved thermal stability, mechanical strength, or electrical conductivity, depending on the application.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-Bromo-2,4-difluoro-benzoic acid is utilized as a versatile starting material for the synthesis of bioactive compounds. Its presence in these compounds can modulate their pharmacological properties, such as potency, selectivity, and bioavailability, leading to the development of more effective therapeutic agents.
Overall, 5-Bromo-2,4-difluoro-benzoic acid is a valuable chemical compound with diverse applications across various industries, including pharmaceuticals, agrochemicals, materials science, and medicinal chemistry. Its unique properties and reactivity make it an essential component in the development of innovative chemical compounds and materials with improved performance and functionality.

Upstream product

• 1583-58-0 2,4-difluoro-benzoic acid 
• 372-18-9 1,3-Difluorobenzene 
• 651027-03-1 (3-bromo-2,6-difluorophenyl)triethylsilane 
• 651027-02-0 1-triethylsilyl-2,6-difluorobenzene 
• 651027-08-6 3-bromo-4,6-difluoro-5-(triethylsilyl)benzoic acid 

Downstream Products

• 869893-92-5 6-(3-chloro-2-fluorobenzyl)-7-fluoro-1-((S)-1-hydroxymethyl-2-methylprop-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 697761-98-1 elvitegravir 
• 934161-52-1 6-bromo-1-((S)-1-tert-butyldimethylsilyloxymethyl-2-methylpropyl)-7-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 953803-84-4 ethyl 6-bromo-4-chloro-7-fluoroquinoline-3-carboxylate 

Relevant academic research and scientific papers

Preparation method of high-purity 5-bromo-2,4-difluorobenzoic acid

The invention discloses a preparation method of high-purity 5- bromine-2,4-difluorobenzoic acid, and belongs to the technical field of synthesis of pharmaceutical and chemical intermediates. Accordingto the preparation method, 2,4-difluorobenzoic acid is reacted with a brominating reagent in sulfuric acid, after the reaction is terminated, the reaction product is esterified with alcohol, rectification and purification is carried out, and treatments such as hydrolysis, acidification and the like are carried out to obtain the high-purity of 5-bromo-2,4-difluorobenzoic acid. According to the preparation method, a solid crude product of 5-bromo-2,4-difluorobenzoic acid is esterified into a liquid, the impurity 3,5-dibromo-2,4-difluorobenzoic acid is separated by distillation, and then hydrolysis is carried out to obtain acid, so that the purity of the product can reach more than 99.5% to meet the requirements of high-quality pharmaceutical intermediates, and the yield is also improved toa certain extent to bring benefit to reduce the production cost and reduce the environmental pollution.

ANTIDIABETIC TRICYCLIC COMPOUNDS

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

ANTIDIABETIC TRICYCLIC COMPOUNDS

Novel compounds of the structural formula (I), and the pharmaceutically acceptable salts thereof, are agonists of G-protein coupled receptor 40 (GPR40) and may be useful in the treatment, prevention and suppression of diseases mediated by the G-protein-coupled receptor 40. The compounds of the present invention may be useful in the treatment of Type 2 diabetes mellitus, and of conditions that are often associated with this disease, including obesity and lipid disorders, such as mixed or diabetic dyslipidemia, hyperlipidemia, hypercholesterolemia, and hypertriglyceridemia.

Exploring Structural Opportunities: The Regioflexible Substitution of 1,3-Difluorobenzene

To demonstrate the superiority of modern organometallic methods, the inexpensive starting material 1,3-difluorobenzene has been selectively converted into the three benzoic acids and all seven bromobenzoic acids containing the two fluorine atoms in homovicinal positions. The 2,6-difluorobenzoic acid (1) was prepared in a one-pot reaction consisting of direct metallation and carboxylation. The key step on the route to the bromobenzoic acid 4 was a deprotonation-triggered bromine migration from the 2- to the 4-position. All other products were attained through (2,6-difluorophenyl)triethylsilane (11). Consecutive deprotonation of the sites adjacent to the fluorine atoms, followed by appropriate electrophilic substitution, provided not only the acid 7 but also the dibromo and iodobromo derivatives 13 and 23. These in turn gave the isomers 14 and 24 upon base-mediated migration of the heaviest halogen, which made the acids 8 and 10 directly accessible. The regiocontrolled monodebromination of intermediate 14 afforded (4-bromo-2,6-difluoro)triethylsilane (15), which opened the route to the acids 3 and 5 (by carboxylation and protodesilylation) and to acid 9 (by carboxylation and bromodesilylation). Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.