ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis and characterization of new benzyl-protected 2-iodo-4-tert-octylphenol and its application in preparation of 1-benzyloxy-2-(3,6-di-tert-butyl-9H-carbazolyl)-4-tert-octylbenzene

Yong-Qing Li, Luo-Yi Wang, Quan-chao Wang, Yu-Cai Hu, Yu-Chen Ci, and Yu-Cai Cao

State Key Laboratory of Polyolefins and Catalysis, Shanghai Key Laboratory of Catalysis Technology for Polyolefins, Shanghai Research Institute of Chemical Industry Co. Ltd., Shanghai, People’s Republic of China

E-mail: caoyc@srici.cn

Received: 26 July 2021  Accepted: 9 September 2021

Abstract:

1-Benzyloxy-2-iodo-4-tert-octylbenzene was synthesized with new methods from 4-tert-octylphenol via bromination, benzyl protection and halogen exchange reaction. Improved yield and easy purification benefit this method. The effects of solvents and ligands in halogen exchange reaction were studied in detail. The synthesized 1-benzyloxy-2-iodo-4-tert-octylbenzene was further examined for its application in Ullmann coupling reaction for preparation of 1-benzyloxy-2-(3,6-di-tert-butyl-9H-carbazolyl)-4-tert-octylbenzene. These newly synthesized compounds were characterized by IR, GC, ¹H NMR, ¹³C NMR, GC–MS and HRMS.

Keywords: Non-metallocene; Halogen exchange; Benzyl protection; Recrystallization

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-021-01867-6

Chemical Papers 76 (1) 287–292 (2022)