This study explores the halogenation of aromatic carboxylic acids through electrophilic aromatic substitution (EAS) and their subsequent use in nucleophilic aromatic substitution (SNAr) reactions, emphasizing the preservation of the carboxylic group (-COOH). The analysis covers reaction mechanisms, empirical and theoretical approaches, and the evolution of these processes from classical methods, such as Br₂/FeBr₃ halogenation, to modern eco-technological innovations like NBS/carborane catalysis and electrochemical SNAr. Classical methods yield 70-90% but are limited by high waste and corrosion, while modern approaches achieve up to 95% selectivity at room temperature with minimal environmental impact. Challenges like decarboxylation and low selectivity are addressed using microwave reactors or pressurized systems. The study provides practical recommendations for selecting optimal synthesis methods based on yield, selectivity, environmental sustainability, and waste minimization, proposing the integration of NBS/carborane and electrochemical SNAr for efficient, eco-friendly organic synthesis.

Aromatic carboxylic acids, electrophilic aromatic substitution, nucleophilic aromatic substitution

Bunnett, J. F. (1962). Investigation of Aromatic Nucleophilic Substitution Reactions. Chemical Reviews, 62(5), 413–433.

Karimov, J. S. (2022). Tiomachevin fragmentini saqlaydigan salitsil kislotasi birikmalarining sintezi. Amerika ijtimoiy va gumanitar tadqiqotlar jurnali, 3(11), 421–427.

Niyazov, L. N., Brel, A. K., Bakhromov, Kh. K., Gapurov, U. U., & Karimov, J. S. (2021). Sintez natrievoj soli proizvodnogo salitsilovoj kisloty. Materialy mezhdunarodnoj nauchno-teoreticheskoj konferencii po teme: “Kuatbekovskie chtenija-1: uroki nezavisimosti”, posvjashhennoj 30-letiju Nezavisimosti Respubliki Kazakhstan.

Chen, Y. et al. (2024). Catalyst-Free Electrochemical Nucleophilic Aromatic Substitution of Fluoroarenes. Chem, 10(2), 456–472.

Karimov, J. S. (2021). Proizvodnye tiomocheviny s gidroksibenzoynymi kislotami. Universum: khimiya i biologiya, (8(86)). URL: https://cyberleninka.ru/article/n/proizvodnye-tiomocheviny-s-gidroksibenzoynymi-kislotami.

Karimov, J. S., & Djunaidov, X. H. (2022). Salitsil kislotaning tiomachevina fragmenti saqlagan birikmalari sintezi tahlili. Kimyo va tibbiyotda: nazariyadan amaliyotgacha, 183–184.

Sobirzoda, K. J. (2022). 4-N Dietil Amino Butin-2 Ol-1 sintez reaktsiyasi mexanizmi. Yevropa jurnali noformal ta'limdagi innovatsionlar, 2(3), 61–67.

Smith, J. et al. (2024). Carborane-Catalyzed Aromatic Halogenation: Green Approaches. Current Opinion in Green and Sustainable Chemistry, 45, 100–115.

Karimov, J. S., & Niyazov, L. N. (2021). Gidroksibenzoik kislotolar bilan tiorea hosulalari. Universum: kimyo va biologiya, (8(86)), 61–63.

Karimov, J. S. (2023). Opredelenie toksichnosti (2S)-2-amino-3-(1H-indol-3-il). Scientific Impulse, 1, 9.

Master Organic Chemistry (2018). Nucleophilic Aromatic Substitution: Mechanisms and Examples. Online resource.