Synthesis
In a 250 mL round bottom flask, 4.0 g (23.3 mmol) of o-bromoaniline, 16.1 g (116.5 mmol) of anhydrous potassium carbonate, 7.3 mL (116.5 mmol) of iodomethane, and 50 mL of acetonitrile were added sequentially. The reaction mixture was heated to 70 °C and stirred at this temperature for 18 hours. Upon completion of the reaction, the mixture was cooled to room temperature. Subsequently, extraction was carried out with 100 mL of deionized water and 100 mL of diethyl ether. After separation of the organic phase, the aqueous phase was further washed with 3 x 50 mL of ether. All organic phases were combined and washed with 5 x 50 mL saturated saline. The organic phase was dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the volatile solvent to obtain the crude product. The crude product was purified by silica gel column chromatography with the eluent of ether/hexane (5/95 v/v), resulting in 2.7 g of light yellow oily liquid product in 69% yield. The characterization data of the obtained product were consistent with those reported in the literature.
References
[1] Organic Letters, 2009, vol. 11, # 22, p. 5130 - 5133
[2] Organic Letters, 2014, vol. 16, # 14, p. 3832 - 3835
[3] Journal of Organic Chemistry, 2008, vol. 73, # 16, p. 6330 - 6340
[4] Patent: CN108586536, 2018, A. Location in patent: Paragraph 0011-0012; 0034-0036; 0038
[5] Chemische Berichte, 1907, vol. 40, p. 2528
