6-BROMO-2,3-DIFLUOROBENZALDEHYDE Chemical Properties

Melting point:

39-43℃

Boiling point:

225.7±35.0 °C(Predicted)

Density 

1.758±0.06 g/cm3(Predicted)

storage temp. 

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

Sensitive 

Air Sensitive

InChI

InChI=1S/C7H3BrF2O/c8-5-1-2-6(9)7(10)4(5)3-11/h1-3H

InChIKey

LAVPYRPTHABUAD-UHFFFAOYSA-N

SMILES

C(=O)C1=C(Br)C=CC(F)=C1F

Safety Information

HS Code 

2913000090

6-BROMO-2,3-DIFLUOROBENZALDEHYDE Usage And Synthesis

Uses

6-BROMO-2,3-DIFLUOROBENZALDEHYDE is a useful research chemical.

Synthesis

General procedure for the synthesis of 6-bromo-2,3-difluorobenzaldehyde from 3,4-difluorobromobenzene and N,N-dimethylformamide: Aryl bromide (1.0 eq.) was dissolved in anhydrous THF (0.2 M) and the reaction mixture was cooled to -78 °C under nitrogen protection. LDA (2.0 M in THF, 1.1 eq.) was added dropwise over 15 min. Stirring was continued for 20 min after addition. DMF (1.2 eq.) was then added and stirred at -78 °C for 15 min. Glacial acetic acid (4.0 eq.) was added, followed immediately by water (12 times the volume of glacial acetic acid) and the reaction mixture was slowly warmed to room temperature. The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic layers were washed sequentially with dilute aqueous HCl, water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel column chromatography with the eluent being a hexane solution of 0 to 5% ethyl acetate to give 6-bromo-2,3-difluorobenzaldehyde (83% yield) as a yellow oil.1H NMR (CDCl3) δ: 7.31 (t, J = 1.4 Hz, 1H), 7.45 (ddd, J = 9.0, 4.1, 1.9 Hz, 1H), 7.29 (td, J = 9.2, 8.0 Hz, 1H).

References

[1] Patent: WO2004/9578, 2004, A2. Location in patent: Page 40
[2] Patent: WO2015/67549, 2015, A1. Location in patent: Page/Page column 122
[3] Patent: US2015/126449, 2015, A1. Location in patent: Paragraph 0676 - 0678
[4] Patent: WO2009/108838, 2009, A1. Location in patent: Page/Page column 67-68

6-BROMO-2,3-DIFLUOROBENZALDEHYDE(360576-04-1)Related Product Information

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