Synthesis
General procedure for the synthesis of 2-bromo-N,N,4-trimethylaniline from N,N-dimethyl-p-toluidine: In a round-bottomed flask, N,N-dimethyl-p-toluidine (1 mmol) was mixed with 48% aqueous hydrobromic acid (1 mL) in dimethyl sulfoxide (DMSO, 1 mL). The reaction mixture was stirred at the indicated temperature for 1-4 hours. After completion of the reaction, it was cooled to room temperature and the pH of the reaction solution was adjusted to 7-8 with 4 M aqueous sodium hydroxide.Subsequently, the reaction mixture was extracted twice with ethyl acetate (EtOAc) and the organic phases were combined. The organic phase was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the target product 2-bromo-N,N,4-trimethylaniline.
References
[1] Journal of Chemical Research, 2014, vol. 38, # 10, p. 593 - 596
[2] Synthesis, 2009, # 21, p. 3672 - 3676
[3] Synthetic Communications, 2010, vol. 40, # 19, p. 2954 - 2962
[4] Tetrahedron Letters, 2007, vol. 48, # 45, p. 7969 - 7973
[5] Chemische Berichte, 1908, vol. 41, p. 2117
