4-(4-Bromo-3-formylphenoxy)benzonitrile
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4-(4-Bromo-3-formylphenoxy)benzonitrile
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CAS No:
906673-54-9
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Formula:
C14H8BrNO2
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Chemical Name:
4-(4-Bromo-3-formylphenoxy)benzonitrile
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Synonyms:
Benzonitrile,4-(4-bromo-3-formylphenoxy)-;4-(4-Bromo-3-formylphenoxy)benzonitrile;1160182-47-7
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CAS No:
4-(4-Bromo-3-formylphenoxy)benzonitrile Use and Manufacturing
In a round bottom flask, under nitrogen atmosphere, 2-bromo-5-hydroxybenzaldehyde (100 g, 497 mmol) and 4-fluorobenzonitrile (301 .2 g, 2487 mmol) were dissolved in DMF (250 ml) and toluene (500 ml). To the resulting dark solution, potassium carbonate (206.2 g, 1492 mmol) was added and the resulting mixture was stirred for 8 hours at 1 15 °C. After the reaction was completed by TLC, the heterogeneous mixture was filtered. The solvents and 4-fluoro-benzonitrile were distilled under reduced pressure from the obtained filtrate. Ethyl acetate (800 ml), water (500 ml) and brine (40 ml) were added and the formed phases were separated at 65-70 °C. The aqueous phase was extracted with ethyl acetate (150 ml) at 65-70 °C and the combined organic phase was washed with a mixture of water (225 ml) and brine (180 ml) at 65-70 °C. The obtained organic phase was evaporated under reduced pressure to give a brown solid. The solid was purified twice by recrystallization in a hot mixture of ethyl acetate and toluene to give 4-(4-bromo-3- formylphenoxy)benzonitrile (compound A) (107.5 g). Yield: 71 percent Purity by HPLC: >99percent A mixture of 2-bromo-5-hydroxybenzaldehyde (50g), 4-fluorobenzonitrile (75.3 lg) and potassium carbonate (103g) in dimethylformamide (500mL) was stirred at about 75°C to about 85°C for about 20h. The reaction mixture was filtered and the filtrate was quenched with water at about room temperature, stirred for about 2h, filtered and dried. The crude product was purified by ethyl acetate. Yield: 50g HPLC purity: >99percent
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4-(4-Bromo-3-formylphenoxy)benzonitrile
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