Synthesis
To a stirred dichloromethane solution (300 mL) of 4-bromobenzoyl chloride (20.0 g, 91.1 mmol) was added triethylamine (28.0 mL, 200.0 mmol) and O,N-dimethylhydroxylamine hydrochloride (9.33 g, 95.6 mmol) at -78 °C. The reaction mixture was slowly warmed to room temperature and stirred continuously for 1.5 hours. After completion of the reaction, the mixture was concentrated to remove the solvent. The residue was ground with acetone and the solid obtained was dissolved in ethyl acetate and washed sequentially with water and brine. The organic layer was dried with anhydrous magnesium sulfate, filtered and concentrated to give 4-bromo-N-methoxy-N-methylbenzamide (18.6 g, 84% yield).
References
[1] Angewandte Chemie - International Edition, 2010, vol. 49, # 17, p. 3073 - 3076
[2] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 17, p. 3694 - 3698
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 46, p. 6840 - 6850
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1415 - 1419
[5] Patent: US2007/66628, 2007, A1. Location in patent: Page/Page column 15
