2-bromo-5-nitrobenzaldehyde

Uses

2-Bromo-5-nitrobenzaldehyde is a cholesteryl ester transfer protein (CETP) inhibitor. 2-Bromo-5-nitrobenzaldehyde is a commonly used reactant for the synthesis of (-)-Linarinic acid derivatives as neuroprotective agents against oxygen glucose deprivation (OGD)-induced cell damage.

Synthesis

2-Bromobenzaldehyde (10.0 g, 53.7 mmol) was dissolved in concentrated sulfuric acid (100 mL) at 0 °C. Potassium nitrate (5.43 g, 53.7 mmol) was added in batches over 1 h at this temperature. After addition, the reaction mixture was continued to be stirred for 40 min, followed by the addition of potassium nitrate (0.72 g). The reaction temperature was maintained at 0°C and stirring was continued for 3 hours. After completion of the reaction, the mixture was slowly poured into ice water. The precipitate precipitated was collected by filtration, washed well with water and finally recrystallized with ethyl acetate/pentane mixed solvent to give 2-bromo-5-nitrobenzaldehyde (11.7 g, 94% yield) as a white solid. The mass spectrometry (ESI) analysis was consistent with the theoretical value of C7H4BrNO3 (228.9).

References

[1] Patent: WO2014/186313, 2014, A1. Location in patent: Page/Page column 173-174
[2] Patent: US2015/152108, 2015, A1. Location in patent: Paragraph 0881; 0882
[3] Tetrahedron Letters, 2016, vol. 57, # 1, p. 11 - 14
[4] Organic and Biomolecular Chemistry, 2017, vol. 15, # 6, p. 1355 - 1362
[5] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 20, p. 5051 - 5057