ChemicalBook CAS DataBase List Methyl 3-cyano-4-Methylbenzoate

Methyl 3-cyano-4-Methylbenzoate synthesis

5synthesis methods

Product Name:Methyl 3-cyano-4-Methylbenzoate
CAS Number:35066-32-1
Molecular formula:C10H9NO2
Molecular Weight:175.18

557-21-1

90347-66-3

35066-32-1

GENERAL METHOD: Methyl 3-iodo-4-methylbenzoate (10.0 mmol), zinc cyanide (10.0 mmol) and tetrakis(triphenylphosphine)palladium (2.0 mmol) were dissolved in 20 mL of N,N-dimethylformamide (DMF). The reaction mixture was heated and stirred at 80 °C for 5 h under nitrogen protection. After completion of the reaction, the mixture was extracted with dichloromethane (25 mL × 3), the organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to obtain the crude product. Finally, the crude product was purified by silica gel column chromatography to obtain the target compound methyl 3-cyano-4-methylbenzoate.

557-21-1 Synthesis

557-21-1
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90347-66-3 Synthesis

90347-66-3
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35066-32-1
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Yield:35066-32-1 78%

Reaction Conditions:

with tetrakis(triphenylphosphine) palladium⁽⁰⁾ in N,N-dimethyl-formamide at 80; for 5 h;Inert atmosphere;

Steps:

General procedure for thesynthesis of Cyanide 3
General procedure: Iodides 2 (10.0 mmol), zinccyanide (10.0 mmol), tetrakis (triphenylphosphine) palladium (2.0 mmol) weredissolved in 20 mL DMF. The reaction was heated at 80 ^oC for 5 hoursunder the protection of N₂. The mixture was extracted with CH₂Cl₂ (25×3 mL) andorganic layers were combined, washed with brine, dried over Na₂SO₄.The solvent was evaporated under vacuum to give crude product, which waspurified by column chromatography on silica gel to give products 3-1~3-3.

References:

Han, Mei;Li, Shan;Ai, Jing;Sheng, Rong;Hu, Yongzhou;Hu, Youhong;Geng, Meiyu [Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,# 23,p. 5679 - 5684] Location in patent:supporting information

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