Uses
5-Bromo-2-methoxy-3-nitropyridine is easily modified, making it a commonly used molecular group for constructing hole transport materials, host materials, and luminescent materials. 5-Bromo-2-methoxy-3-nitropyridine not only possesses a large π-electron conjugation system, strong electron transfer capability, and a rigid fused-ring structure, but its pyridine ring also readily incorporates various functional groups. This makes 5-Bromo-2-methoxy-3-nitropyridine widely applicable in OLED devices, exhibiting significant performance characteristics in different functional layers. Consequently, research in this field is very active, yielding many important results.
Synthesis
Sodium metal (2.90 g, 126.4 mmol) was added to the cooled methanol (50.0 mL) in batches, and the mixture was slowly warmed to room temperature with continuous stirring until the sodium was completely dissolved. Subsequently, the solution was added to 2-chloro-3-nitro-5-bromopyridine (10.0 g, 42.12 mmol, Shanghai Longsheng Chemical, China) suspended in methanol (100 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 1 hour, then warmed up to room temperature and continued stirring for 16 hours. Upon completion of the reaction, the mixture was concentrated to about 80 mL and the reaction was quenched with deionized water (100 mL). The precipitate was collected by filtration, washed with deionized water (50 mL x 2) and dried under an infrared lamp to afford 5-bromo-2-methoxy-3-nitropyridine as a light yellow solid (9.62 g, 98% yield). Mass spectrum (ESI, positive ion mode) m/z: 233.0 [M + H]+.
References
[1] Patent: US2014/134133, 2014, A1. Location in patent: Paragraph 0384
[2] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 15, p. 3534 - 3541
[3] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 7, p. 737 - 741
[4] Patent: WO2014/22128, 2014, A1. Location in patent: Paragraph 0149
