ChemicalBook CAS DataBase List 2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile

2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile synthesis

9synthesis methods

Product Name:2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile
CAS Number:763114-25-6
Molecular formula:C16H8FNO2
Molecular Weight:265.24

(3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphonic acid (5.00 g, 0.021 mol) in tetrahydrofuran (30 mL) was added to a 150 mL round-bottom flask. To this solution, triethylamine(5.6 mL, 0.042 mol) was added. 2-Fluoro-5-formyl benzonitrile( 3.08 g, 0.021 mol) was dissolved in tetrahydrofuran into another round-bottom flask, followed by adding triethylamine (2.9 mL, 0.021 mol) and stirring evenly. Then the reaction fluids in the two flasks were mixed and reacted at room temperature for 12 h. The product was concentrated under reduced pressure and 50 mL of water was added. The suspension was stirred for 30 min until the solids were not precipitated. Finally, filtration was performed, and the filter cake was collected and dried to obtain 2-Fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-benzonitrile(5.41 g, 97%).

2-Fluoro-5-[(3-oxo-1(3H)-isobenzofuranylidene)methyl]-benzonitrile

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61260-15-9 Synthesis

3-oxo-1,3-dihydroisobenzofuran-1-ylphosphonic acid

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2-Fluoro-5-((3-oxoisobenzofuran-1(3H)-ylidene)methyl)benzonitrile

763114-25-6
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Yield:763114-25-6 202.3 g

Reaction Conditions:

with triethylamine for 1 h;

Steps:

4-6

2) 252.92 g of TEA was added to the prepared reaction solution containing compound III, 163.90 g of IIb was added in batches, and the reaction was carried out for 1 h. The reaction was monitored by HPLC, and the content of Compound III was less than 5% as the end of the reaction;The resulting reaction solution was suction filtered, rinsed with anhydrous methanol, the filter cake was added to 3000 ml of water, stirred, and the temperature was controlled at 30°C, and stirred for 1 h. Suction filtration, rinsed with water, and air-dried at 60°C to obtain compound IV 202.03g, yield 76.2%, purity 99.87%, total impurities 0.13%, unknown maximum single impurities 0.05%.

References:

CN114075159,2022,A Location in patent:Paragraph 0030; 0117-0136

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218301-22-5 Synthesis