4-bromo-2,5-difluorobenzaldehyde Chemical Properties

Boiling point:

237℃

Density 

1.758

Flash point:

97℃

storage temp. 

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

form 

crystalline solid

color 

Off white to faint yellow

Safety Information

HS Code 

2913000090

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

Synthesis

Example 31 Preparation of 4-bromo-2,5-difluorobenzaldehyde To a solution of 2,5-dibromo-1,4-difluorobenzene (10.0 g, 36.77 mmol) in ether (150 mL) was added slowly and dropwise to butyllithium (2.5 M hexane solution, 14.86 mL, 37.15 mmol) at -78 °C under nitrogen protection. The reaction mixture was stirred at -78 °C for 30 min. Subsequently, a solution of anhydrous N,N-dimethylformamide (3.13 mL, 40.46 mmol) in ether (10 mL) was added dropwise and the reaction system was slowly warmed to room temperature over a period of 2 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution (25 mL) and extracted with ether. The organic phases were combined, washed with saturated brine solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure (note: the product is highly volatile). The crude product was purified by fast column chromatography (silica gel as stationary phase, eluent 2-20% ethyl acetate in hexane solution) to afford the title compound 4-bromo-2,5-difluorobenzaldehyde as a light yellow solid (7.0 g, 86% yield). 1H NMR (400 MHz, CDCl3): δ 7.50 (dd, J = 5.08,8.92 Hz, 1H), 7.62 (dd, J = 5.80,7.68 Hz, 1H), 10.30 (d, J = 2.76 Hz, 1H).

References

[1] Patent: US2014/274696, 2014, A1. Location in patent: Paragraph 0289; 0290
[2] Patent: US2014/200215, 2014, A1. Location in patent: Paragraph 1205; 1206
[3] Patent: WO2013/74641, 2013, A1. Location in patent: Paragraph 00350
[4] Patent: WO2012/149413, 2012, A1. Location in patent: Page/Page column 63
[5] Patent: US2010/222345, 2010, A1. Location in patent: Page/Page column 97

4-bromo-2,5-difluorobenzaldehyde(357405-75-5)Related Product Information

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