Synthesis
GENERAL METHOD: To a reaction tube containing N-bromosuccinimide (NBS, 1.5 eq, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and acetonitrile (CH3CN, 1.0 mL) was added 3-chloroanisole (1a, 0.2 mmol). The reaction mixture was stirred for 12 h at room temperature in a dark environment. Upon completion of the reaction, the reaction was quenched by the addition of 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, v/v) as eluent to give the target product 4-bromo-3-chloroanisole (2a).
References
[1] Synthetic Communications, 2007, vol. 37, # 2, p. 323 - 328
[2] Tetrahedron, 2017, vol. 73, # 50, p. 7105 - 7114
[3] Journal of the Serbian Chemical Society, 2011, vol. 76, # 5, p. 685 - 692
[4] Monatshefte fur Chemie, 2013, vol. 144, # 2, p. 179 - 181
