Preparation
1-Bromopyrene is an important intermediate in the OLED material industry. The synthesis method is as follows: pyrene is dissolved in an organic solvent dichloromethane, and dibromohydantoin is added for reaction, filtered, and the obtained solid is recrystallized to obtain 1-bromopyrene.
Synthesis
The general procedure for the synthesis of 1-bromopyrene from pyrene was as follows: anhydrous N,N-dimethylformamide (DMF, 5 mL) solution of N-bromosuccinimide (NBS, 187 mg, 1.05 mmol) was slowly added dropwise to anhydrous DMF (10 mL) solution of pyrene (252 mg, 1.0 mmol) and the reaction mixture was stirred at room temperature for 24 hours. After completion of the reaction, the mixture was poured into deionized water (50 mL) and extracted three times with dichloromethane (100 mL). The organic phases were combined, washed thoroughly with deionized water, dried over anhydrous magnesium sulfate (MgSO4), and concentrated under reduced pressure to remove the solvent to give the crude product 1-bromopyrene (332 mg, 85% yield) as a light yellow solid. The crude product was recrystallized with hexane to obtain pure 1-bromopyrene as light yellow powder, melting point 103-104°C (literature value: 102-104°C).
References
[1] Tetrahedron Letters, 2010, vol. 51, # 9, p. 1317 - 1321
[2] Journal of the Chinese Chemical Society, 2012, vol. 59, # 3, p. 289 - 296
[3] Tetrahedron Letters, 2003, vol. 44, # 21, p. 4085 - 4088
[4] European Journal of Organic Chemistry, 2011, # 27, p. 5261 - 5271
[5] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2013, vol. 68, # 4, p. 367 - 377
