Synthesis
Isophthalic acid (10 g, 60 mmol) and concentrated sulfuric acid (60 mL, 98%) were added to a 100 mL round-bottomed flask and stirred until completely dissolved. N-bromosuccinimide (12.8 g, 72 mmol) was added in batches in an oil bath at 60 °C, and the addition time was kept within 10 min. The reaction mixture was stirred at 60 °C overnight. Upon completion of the reaction, it was cooled to room temperature and the reaction was quenched by addition of water/ice mixture. The precipitate was collected by filtration and washed with hexane (2 x 60 mL). The solid was dried in an oven under reduced pressure. The crude product was purified by recrystallization from ethyl acetate to give 5-bromoisophthalic acid (3 g, 20% yield) as a white solid.
References
[1] Tetrahedron, 2001, vol. 57, # 24, p. 5027 - 5038
[2] Tetrahedron Letters, 2000, vol. 41, # 7, p. 1015 - 1018
[3] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[4] Patent: US6689922, 2004, B1. Location in patent: Page column 40-41
[5] Patent: US2015/152123, 2015, A1. Location in patent: Paragraph 0156; 0157; 0158
