Facile p-toluenesulfonic acid-promoted para-selective monobromination and chlorination of phenol and analogues

• Main Authors: Pakorn Bovonsombat, Rameez Ali, Chiraphorn Khan, Juthamard Leykajarakul, Kawin Pla-On, Suraj Aphimanchindakul, Natchapon Pungcharoenpong, Nisit Timsuea, Anchalee Arunrat, Napat Punpongjareorn
• Other Authors: Mahidol University
• Format: Article
• Published: 2018
• Subjects: Biochemistry, Genetics and Molecular Biology; Chemistry; Pharmacology, Toxicology and Pharmaceutics
• Online Access: https://repository.li.mahidol.ac.th/handle/123456789/28654

para-Regioselective bromination of phenol and analogues, promoted by p-toluenesulfonic acid, is achieved in high to excellent yields at room temperature with N-bromosuccinimide. Chlorination with N-chlorosuccinimide and catalysed by p-toluenesulfonic acid also gives para-chlorinated phenol analogues in good yields at room temperature. para-Bromination of phenol, promoted by p-toluenesulfonic acid, is achieved in excellent yields at room temperature with N-bromosuccinimide. p-Toluenesulfonic acid is also effective as a promoter of para-chlorination with N-chlorosuccinimide. © 2010 Elsevier Ltd. All rights reserved.