3-Bromo-5-nitrobenzaldehyde

Uses

3-Fluoro-5-nitrobenzaldehyde is used as a reactant in the design and synthesis of selective activators of cardiac myosin.

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 5867, 2007 DOI: 10.1021/jo070477u

Synthesis

General procedure for the synthesis of 3-bromo-5-nitrobenzaldehyde from m-nitrobenzaldehyde: 3-nitrobenzaldehyde (1.0 g, 6.6 mmol) was dissolved in concentrated sulfuric acid (4.0 mL) at room temperature, followed by batchwise addition of N-bromosuccinimide (1.4 g, 7.9 mmol). The reaction mixture was heated to 65 °C and maintained at this temperature for 1 hour. After completion of the reaction, it was cooled to room temperature and the reaction solution was slowly poured into ice water, the solid was precipitated and collected by filtration. The crude product was dried with anhydrous sodium sulfate and purified by recrystallization through a solvent mixture of ethyl acetate/petroleum ether (1:10, v/v) to finally obtain 3-bromo-5-nitrobenzaldehyde (1.3 g, 82% yield) as white crystals. The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 10.09 (s, 1H), 8.79-8.55 (m, 2H), 8.51 (s, 1H).

References

[1] Journal of Medicinal Chemistry, 2018, vol. 61, # 12, p. 5235 - 5244
[2] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[3] European Journal of Medicinal Chemistry, 2016, vol. 116, p. 46 - 58
[4] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4512 - 4513
[5] Patent: WO2009/153313, 2009, A1. Location in patent: Page/Page column 185