
Methyl 3-cyano-4-Methylbenzoate synthesis
- 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.
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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