3-BROMO-5-METHOXYBENZALDEHYDE Chemical Properties

Melting point:

45-46 °C

Boiling point:

279.5±20.0 °C(Predicted)

Density 

1.522±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

solid

color 

Off-white to yellow

Safety Information

HS Code 

2913000090

3-BROMO-5-METHOXYBENZALDEHYDE Usage And Synthesis

Uses

3-Bromo-5-methoxybenzaldehyde, can be used for the synthesis of novel scaffold, that led to the discovery of potent and selective Inhibitors of Dihydrofolate Reductase, used for the treatment of Cryptosporidiosis. It can also be used for the synthesis of Tetrahydrobenzoxepino[2,3,4-ij]isoquinolines derivatives, as Dopamine Receptor ligands.

Synthesis

Example 1 5A: Synthesis of 3-bromo-5-methoxybenzaldehyde 3-Bromo-5-hydroxybenzaldehyde (0.5 g, 2.487 mmol) was dissolved in N,N-dimethylformamide (DMF, 14.63 mL) and the solution was cooled to 0 °C. Under stirring, sodium hydride (NaH, 0.119 g, 4.97 mmol) was added in three batches. Subsequently, the reaction mixture was slowly warmed to room temperature and iodomethane (MeI, 0.933 mL, 14.92 mmol) was added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction mixture was diluted with water and partially concentrated under reduced pressure. The concentrate was diluted with dichloromethane (DCM), washed twice sequentially with water and once with saturated brine, and then dried over anhydrous sodium sulfate (Na2SO4). After filtration to remove the desiccant, the filtrate was concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography with an elution gradient of 0 to 100% ethyl acetate (EtOAc) in hexane solution to give the title compound Example 15A (0.488 g, 2.27 mmol, 9% yield). 1H NMR (400 MHz, chloroform-d) δ 9.91 (1H, s), 7.58 (1H, t, J = 1.38 Hz), 7.28-7.35 (2H, m), 3.86 (3H, s).

References

[1] Patent: WO2014/201073, 2014, A1. Location in patent: Paragraph 00295
[2] ACS Medicinal Chemistry Letters, 2017, vol. 8, # 1, p. 67 - 72