5-Bromo-2,4-difluorobenzaldehyde Chemical Properties

Boiling point:

229.4±35.0 °C(Predicted)

Density 

1.758±0.06 g/cm3(Predicted)

storage temp. 

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

form 

fused solid

color 

Faint lemon

Safety Information

HS Code 

2913000090

5-Bromo-2,4-difluorobenzaldehyde Usage And Synthesis

Uses

5-Bromo-2,4-difluorobenzaldehyde is a fluorobenzaldehyde analogue, commonly used as a pharmaceutical intermediate.

Synthesis

General procedure for the synthesis of 5-bromo-2,4-difluorobenzaldehyde from 1,5-dibromo-2,4-difluorobenzene and N,N-dimethylformamide: 1,5-dibromo-2,4-difluorobenzene (17.5 g, 64.2 mmol) was dissolved in ether (100 mL) at -78 °C, and n-butyllithium (2.5 M, 30.8 mL, 77 mmol) was added slowly (2.5 M, 30.8 mL, 77 mmol), over a period of 5 minutes. The reaction mixture was continued to be stirred at -78 °C for 30 min. Subsequently, N,N-dimethylformamide (9.94 mL, 148 mmol) was added all at once and the mixture was stirred at the same temperature for another 30 minutes. After completion of the reaction, the reaction mixture was treated with ethyl acetate and saturated sodium bicarbonate solution. The crude product was purified by silica gel column chromatography using 0-10% ethyl acetate/hexane as eluent to afford the target compound 5-bromo-2,4-difluorobenzaldehyde as a light yellow oil (8.5 g, 60% yield). The product was characterized by 1H NMR (400 MHz, chloroform-d): δ10.26 (s, 1H), 8.14 (t, J=7.5 Hz, 1H), 7.05 (dd, J=9.8,8.0 Hz, 1H).

References

[1] Patent: US2011/9395, 2011, A1. Location in patent: Page/Page column 22
[2] Patent: WO2012/162334, 2012, A1. Location in patent: Page/Page column 38-39
[3] Patent: WO2014/98831, 2014, A1. Location in patent: Page/Page column 27

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