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.
Halogenation And Nucleophilic Aromatic Substitution Reactions Of Aromatic Carboxylic Acids
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References
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