General procedure for the synthesis of 3-bromo-4-nitroanisole from 5-methoxy-2-nitrobenzoic acid: silver sulfate (6.2 mg), copper acetate (36.3 mg), 2,9-dimethyl-1,10-o-phenanthroline (12.5 mg), 5-methoxy-2-nitrobenzoic acid (39.4 mg), and sodium bromide (30.9 mg), followed by the addition of 4 mL of dimethyl sulfoxide (DMSO) as solvent. The reaction mixture was heated to 160°C under oxygen atmosphere and stirred for 24 hours. After completion of the reaction, the reaction was quenched by the addition of distilled water and extracted three times with ethyl acetate (10 mL each time). The organic phases were combined and concentrated to afford 3-bromo-4-nitroanisole (20.4 mg) in 44% yield.
[1] Journal of Organic Chemistry, 2016, vol. 81, # 7, p. 2794 - 2803
[2] Patent: CN107325002, 2017, A. Location in patent: Paragraph 0133
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 30, p. 5416 - 5421
[4] Tetrahedron Letters, 2010, vol. 51, # 50, p. 6646 - 6648
