95740-49-1

39538-68-6

95740-49-1

General procedure for the synthesis of 2-bromo-5-methylanisole from 2-methoxy-4-methylaniline: under nitrogen protection, copper bromide (4.88 g, 21.8 mmol) was dissolved in acetonitrile (20 ml), ethyl nitrite (2.13 ml, 17.9 mmol) was added, and the reaction system was subsequently slowly heated up to 65 °C and maintained. A solution of 2-methoxy-4-methylaniline (2.24 g, 16.3 mmol) in acetonitrile (20 ml) was slowly added to the above reaction mixture and stirring was continued for 15 minutes. After completion of the reaction, the solvent was removed by vacuum distillation, the residue was dissolved in cyclohexane, washed sequentially with 3 x 3 NH3 aqueous solution and water, and the organic phase was dried with anhydrous Na2SO4. The solvent was again removed by vacuum distillation, and the resulting crude product was purified by fast chromatography (with chloroform as eluent) to afford the target product 2-bromo-5-methylanisole (1.92 g, 59% yield).1H-NMR (CDCl3) δ: 2.32 (s, 3H), 3.86 (s, 3H), 6.64 (dd, J = 8.0,1.4 Hz, 1H) , 6.72 (d, J = 1.4Hz, 1H), 7.39 (d, J = 8.0Hz, 1H). 13C-NMR (CDCl3) δ: 21.4,56.1,108.3,113.1,122.5,132.9,138.7,155.6.