Synthesis
The general procedure for the synthesis of 1-pyrenylboronic acid from trimethyl borate and 1-bromopyrene was as follows: 1-bromopyrene (30 g, 107 mmol) was added to a round-bottom flask and dissolved in 240 mL of tetrahydrofuran (THF). Under cooling conditions, n-BuLi (1.6 M, 80 mL) in hexane was slowly added dropwise, keeping the reaction temperature at -78 °C. After the dropwise addition was completed, the reaction mixture continued to be stirred at -78 °C for about 1 hour. Subsequently, trimethyl borate (15.5 g, 149 mmol) was added and stirring was continued at -78 °C for 1 hour. After that, the reaction mixture was warmed up to room temperature and stirred for about 2 hours. After completion of the reaction, the reaction solution was adjusted to acidic with 2N HCl. Extraction was carried out with ethyl acetate (EA) and hexane, and the organic phases were combined and concentrated under reduced pressure to remove the solvent to give 19.5 g of 1-pyrenylboronic acid in 74% yield.
References
[1] Patent: KR101515814, 2015, B1. Location in patent: Paragraph 0343; 0344
[2] Patent: KR101503771, 2015, B1. Location in patent: Paragraph 0215; 0216
[3] Patent: US2014/131664, 2014, A1. Location in patent: Paragraph 0025-0026
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1998, # 7, p. 1263 - 1268
[5] ChemPlusChem, 2013, vol. 78, # 10, p. 1288 - 1295
