2,3-DIFLUORO-4-BROMOBENZALDEHYDE Chemical Properties

Melting point:

66-67℃

storage temp. 

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

form 

Powder

color 

Off-white

Water Solubility 

Slightly soluble in water.

InChI

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

InChIKey

IMOLPSNRLZLWQR-UHFFFAOYSA-N

SMILES

C(C1C=CC(Br)=C(F)C=1F)=O

Safety Information

HS Code 

2913000090

2,3-DIFLUORO-4-BROMOBENZALDEHYDE Usage And Synthesis

Uses

4-Bromo-2,3-difluorobenzaldehyde is used as pharmaceutical intermediates.

Synthesis

1. Preparation of iso-PrMgCl-LiCl complex: LiCl (4.56 g, 107.6 mmol) was placed under high vacuum and dried using a hot air gun for 10 min. Under nitrogen atmosphere, iso-PrMgCl (53.8 mL, 107.6 mmol, 2M THF solution) was added to the dried LiCl, and the reaction mixture was stirred at 23 °C for 3 days to obtain a THF solution of iso-PrMgCl-LiCl complex. 2. Synthesis of 4-bromo-2,3-difluorobenzaldehyde: A THF (5 mL) solution of 1,4-dibromo-2,3-difluorobenzene (1.29 mL, 10 mmol) was slowly added to a solution of the iso-PrMgCl-LiCl complex (5.5 mL, 11 mmol, 2.0 M THF solution) at -40 °C, making sure that the reaction temperature was maintained at below -30 °C . Subsequently, the reaction mixture was stirred at -35 to -30 °C for 1 h. The reaction was then warmed up to -7 °C to continue the reaction for 1 h. The reaction mixture was then cooled to -7 °C to continue the reaction. 3. The reaction mixture was cooled to -30 °C and N,N-dimethylformamide (DMF, 1.00 mL, 13 mmol) was added in a single addition, at which point the temperature rose to -23 °C. The reaction mixture was stirred in the range of -25 to 15 °C for 3.5 hours. 4. Post-treatment: the reaction mixture was poured into a mixture of 1 M H2SO4 and ice, saturated with solid NaCl and extracted twice with methyl tert-butyl ether (MTBE). The organic phases were combined, dried with MgSO4, filtered and concentrated in vacuum to give 4-bromo-2,3-difluorobenzaldehyde (D-1d) 2.17 g in 98% yield as a white solid.

References

[1] Patent: US2008/249151, 2008, A1. Location in patent: Page/Page column 16; 23
[2] Patent: US2009/170856, 2009, A1. Location in patent: Page/Page column 26
[3] Patent: US2006/25462, 2006, A1. Location in patent: Page/Page column 11; 21
[4] Patent: US2006/223874, 2006, A1. Location in patent: Page/Page column 5; 9
[5] Patent: WO2018/75871, 2018, A1. Location in patent: Page/Page column 64-65

2,3-DIFLUORO-4-BROMOBENZALDEHYDE (644985-24-0)Related Product Information

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