5-(2-METHYL-4-NITROPHENYL)-2-FURALDEHYDE synthesis
- Product Name:5-(2-METHYL-4-NITROPHENYL)-2-FURALDEHYDE
- CAS Number:329222-70-0
- Molecular formula:C12H9NO4
- Molecular Weight:231.2
Yield:-
Reaction Conditions:
with [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II);potassium carbonate in ethylene glycol dimethyl ether;ethanol;lithium hydroxide monohydrate; for 8 h;Inert atmosphere;Reflux;Suzuki-Miyaura Coupling;
Steps:
General procedure: 1-bromo-4-methyl-2-nitrobenzene (200mg, 926μmol) and (5-formylfuran-2-yl)boronic acid (155mg, 1.11mmol) were mixed in 2mL dimethoxyethane, 1mL ethanol and 1mL water followed by the addition of Pd(PPh3)2Cl2 (65mg, 92.6μmol) and K2CO3 (256mg, 1.85mmol). The mixture was heated at reflux under the protection of nitrogen for 8h and then cooled to room temperature. The mixture was diluted with water and extracted with ethyl acetate three times. The combined organic phase was dried over anhydrous Na2SO4 and concentrated to give a crude product, which was purified by silica gel column chromatography to get 82mg, yield: 38.3%.
References:
Yuan, Xinrui;Jiang, Hua;Fu, Denggang;Robida, Aaron;Rajanayake, Krishani;Yuan, Hebao;Wen, Bo;Sun, Duxin;Watch, Brennan T.;Chinnaswamy, Krishnapriya;Stuckey, Jeanne A.;Paczesny, Sophie;Rech, Jason C.;Yang, Chao-Yie [Bioorganic and Medicinal Chemistry,2022,vol. 71,art. no. 116942]
