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ChemicalBook CAS DataBase List 4-Chloro-3-nitrotoluene
89-60-1

4-Chloro-3-nitrotoluene synthesis

13synthesis methods
4-METHYL-2-NITROBENZOIC ACID

27329-27-7

4-Chloro-3-nitrotoluene

89-60-1

General procedure for the synthesis of 1-chloro-4-methyl-2-nitrobenzene from 4-methyl-2-nitrobenzoic acid: 6.2 mg of silver sulfate, 36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline, 36.2 mg of 4-methyl-2-nitrobenzoic acid, and 17.5 mg of sodium chloride were added sequentially to a Silak reactor tube fitted with a magnetic stirrer. NaCl, followed by the addition of 4 mL of dimethyl sulfoxide as solvent. The reaction mixture was heated and stirred at 160 °C for 24 hours under an oxygen atmosphere. Upon completion of the reaction, the reaction was quenched by the addition of appropriate amount of distilled water and extracted three times with ethyl acetate (10 mL each time). The organic phases were combined and concentrated under reduced pressure to give 17.5 mg of 1-chloro-4-methyl-2-nitrobenzene in 51% yield.

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Yield: 51%

Reaction Conditions:

with 2.9-dimethyl-1,10-phenanthroline;oxygen;copper (I) acetate;silver sulfate;sodium chloride in dimethyl sulfoxide at 160; for 24 h;Schlenk technique;

Steps:

20 Example 20. Synthesis of 2-nitro-4-methyl chlorobenzene.
Silak reaction tube equipped with a magnetic stirrer was charged with 6.2 mg of silver sulfate,36.3 mg of copper acetate, 12.5 mg of 2,9-dimethyl-1,10-o-phenanthroline,36.2 mg of 2-nitro-4-methylbenzoic acid and 17.5 mg of sodium chloride4 mL of dimethyl sulfoxide.The reaction was heated at 160 ° C for 24 hours in the presence of oxygen.After the reaction was completed, distilled water was added to quench the reaction,Extraction with ethyl acetate 3 times, each time 10mL,The combined organic phases are concentrated,17.5 mg of 2-nitro-4-methylchlorobenzene was obtained,The yield is 51%.

References:

Nanchang University;Fu Zhengjiang;Cai Hu;Li Zhaojie;Jiang Ligao CN107325002, 2017, A Location in patent:Paragraph 0091

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