Uses
5-Bromo-2-methoxybenzonitrile can be used as an organic and pharmaceutical intermediate. Halogenated benzonitrile is an important organic intermediate, mainly used in the preparation of pharmaceuticals and pesticides, and has wide applications in the manufacture of dyes, engineering plastics, and photosensitive materials.
Synthesis
General procedure for the synthesis of 2-methoxy-5-bromobenzonitrile from 2-methoxybenzonitrile: N-bromosuccinimide (NBS, 1.5 eq., 0.3 mmol), catalyst (10 mol%, 0.02 mmol), and acetonitrile (CH3CN, 1.0 mL) were added to the reaction tube, followed by 2-methoxybenzonitrile (0.2 mmol). The reaction mixture was stirred for 12 h at room temperature protected from light. Upon completion of the reaction, the reaction was quenched with saturated sodium thiosulfate (Na2S2O3) aqueous solution (2 mL). The reaction mixture was extracted with ethyl acetate (3.5 mL). The organic phases were combined, washed with brine (10 mL), dried over anhydrous sodium sulfate (Na2SO4) and filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure and the residue was purified by rapid chromatography on a silica gel column using petroleum ether/dichloromethane (5:1) as eluent to afford the target product 2-methoxy-5-bromobenzonitrile.
References
[1] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114
[2] Patent: US2009/203657, 2009, A1. Location in patent: Page/Page column 51
[3] Patent: US2009/203677, 2009, A1. Location in patent: Page/Page column 54
[4] Patent: US2009/197871, 2009, A1. Location in patent: Page/Page column 53-54
[5] Patent: WO2009/100169, 2009, A1. Location in patent: Page/Page column 132-133
