4-(4-Bromo-3-formyl-phenoxy)-benzonitrile Chemical Properties

Melting point:

109-111°C

Boiling point:

441.9±35.0 °C(Predicted)

Density 

1.56±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

White to Light Yellow

InChI

InChI=1S/C14H8BrNO2/c15-14-6-5-13(7-11(14)9-17)18-12-3-1-10(8-16)2-4-12/h1-7,9H

InChIKey

IEHZPKWXBVTRRG-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=C(OC2=CC=C(Br)C(C=O)=C2)C=C1

4-(4-Bromo-3-formyl-phenoxy)-benzonitrile Usage And Synthesis

Uses

4-(4-Bromo-3-formyl-phenoxy)-benzonitrile can be used as organic synthesis intermediate and pharmaceutical intermediate, mainly used in laboratory research and development process and chemical production process.

Synthesis

Under nitrogen protection, 2-bromo-5-hydroxybenzaldehyde (100 g, 497 mmol) and 4-fluorobenzonitrile (301.2 g, 2487 mmol) were dissolved in a mixed solvent of N,N-dimethylformamide (DMF, 250 mL) and toluene (500 mL). Potassium carbonate (206.2 g, 1492 mmol) was added to this dark solution and the reaction mixture was stirred at 115 °C for 8 hours. Upon completion of the reaction, the reaction endpoint was confirmed by thin layer chromatography (TLC) monitoring. Insoluble material was removed by filtration followed by removal of solvent and excess 4-fluorobenzonitrile by distillation under reduced pressure. Ethyl acetate (800 mL), water (500 mL) and brine (40 mL) were added to the residue and phase separation was carried out at 65-70 °C. The aqueous phase was extracted with ethyl acetate (150 mL) at the same temperature and the combined organic phases were washed sequentially with mixed water (225 mL) and brine (180 mL) at 65-70 °C. The organic phase was concentrated under reduced pressure to give a brown solid product. The solid was purified by twice recrystallization in a mixture of hot ethyl acetate and toluene solvents to give 4-(4-bromo-3-formylphenoxy) benzyl cyanide (Compound A) (107.5 g) in 71% yield. High performance liquid chromatography (HPLC) analysis showed purity greater than 99%. Nuclear magnetic resonance hydrogen spectrum (1H-NMR, 200 MHz, CDCl3, δ ppm): 10.32 (1H, s); 7.62-7.72 (3H, m); 7.57-7.59 (1H, dd; J = 3 Hz, J = 1 Hz); 7.18-7.23 (1H, dd, J = 8 Hz, J = 3 Hz), 7.01-7.08 ( 2H, m). Nuclear magnetic resonance carbon spectrum (13C-NMR, 50 MHz, CDCl3, δ ppm): 190.69; 160.08; 155.13; 135.59; 134.89; 134.39; 126.86; 121.81; 120.28; 118.68; 118.33; 107.32. differential scanning calorimetry (DSC) Showed a heat absorption peak at 11.19°C.

References

[1] Patent: WO2018/115362, 2018, A1. Location in patent: Paragraph 0120
[2] Patent: US2007/72833, 2007, A1. Location in patent: Page/Page column 20
[3] Patent: WO2018/224923, 2018, A1. Location in patent: Paragraph 0167; 0181

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