22433-89-2

4-Bromo-1,3-benzenediarbonitrile is a useful reactant for the preparation of di(arylthienyl)thiazolothiazole.

4-Bromoisophthalamide (868 mg, 3.6 mmol) was used as a starting material, and phosphoryl chloride (4 mL) and 1 drop of DMF were added. the reaction mixture was heated and stirred at 90 °C for 1.5 h. The reaction mixture was then cooled to room temperature and stirred for 10 minutes. Upon completion of the reaction, it was cooled to room temperature and the reaction solution was slowly added dropwise onto ice and stirring was continued for 10 min. Subsequently, the resulting solid product was collected by filtration and washed well with cold water. Finally, the product was dried under high vacuum to afford 4-bromoisophthalonitrile as a white solid (671 mg). The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.59-8.56 (m, 1H), 8.15-8.08 (m, 2H).

[1] Journal of Materials Chemistry C, 2015, vol. 3, # 28, p. 7345 - 7355
[2] Journal of Organic Chemistry, 1970, vol. 35, p. 287 - 295
[3] Patent: WO2013/142266, 2013, A1. Location in patent: Paragraph 00529