4-Nitrophenyl phenyl ether preparation

Figure 2. Preparation of 4-nitrophenyl phenyl ether from sodium phenoxide and 4-chIoronitrobenzene using 5 mole % catalyst in chlorobenzene at reflux.

MeTHF has also been used as an alternative to dichloromethane in biphasic reactions including alkylations, amidations and nucleophilic substitutions. For example, 2-nitrophenyl phenyl ether was prepared in 95% yield using 2-MeTHF as the organic solvent through reaction of phenol and o-fluoronitrobenzene using tetrabutylammonium bromide as a phase transfer catalyst. 

PROBLEM 24.9 Which of the following two combinations of reactants is more appropriate for the preparation of p-nitrophenyl phenyl ether ... 

When (3-substituted phenyl)aminomethylenemaIonate (1163, 3-R = H) was applied, a mixture of 5-substituted and 7-substituted 4-hydroxyquino-lines (1164, 5-R + H and 7-R + H) was obtained. For example, the thermal cyclization of (3-nitrophenyl)aminomethylenemalonate in dibenzyl ether at 250°C afforded a 3 1 mixture of 7-nitro- and 5-nitro-4-hydroxy-quinolines (1164, R = 7-N02 and 5-NO ). 4-Hydroxyquinolines (1164) could also be prepared when a mixture of anilines, triethyl orthoformate, and isopropylidene malonate was slowly heated to 100°C in Dowtherm A, stirred over a period of 30 minutes, and then raised to a temperature of... 

Solubility soluble in many organic solvents (dimethylsulfox-ide, dimethylformamide, ethyl acetate, chloroform, dichloro-methane, benzene) slightly soluble in THE, methyl ferf-butyl ether, diethyl ether, and EtOH almost insoluble in water. Preparative Methods CPTTOH and a number of closely related derivatives thereof, such as 4-(/ -methox3q)henyl)-,4-(p-methylphenyl)-, 4-phenyl-, and 4-(/ -nitrophenyl)-substituted 7V-hydroxythiazole-2(3i thione, A-hydroxy-4-methylthia-zole-2(3//) thione (commercially available), and TV-hydroxy-4-methyl-5-(/>-methox) henyl)thiazole-2(377) thione are prepared from the corresponding a-haloketones in three synthetic... 

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