General procedure for the synthesis of 4-bromo-2-nitrobenzyl bromide from 4-bromo-2-nitrotoluene: (1) Preparation of 4-bromo-1-(bromomethyl)-2-nitrobenzene (0145): 4-bromo-2-nitrotoluene (25.0 g, 116 mmol), N-bromosuccinimide (28.2 g, 162 mmol) and 2 ,2'-azobis(2-methylpropionitrile) (1.90 mg, 11.6 mmol) and the reaction mixture was refluxed for 18 hours. After completion of the reaction, the reaction solution was filtered and the filtrate was concentrated under reduced pressure. The resulting crude product was purified by silica gel column chromatography (ethyl acetate/hexane = 1/9) to afford 18.5 g (54% yield) of 4-bromo-2-nitrobenzyl bromide.1H-NMR (CDCl3) data: δ 4.78 (s, 2H, CH2), 7.46 (d, J = 8.0 Hz, 1H, Ar-H), 7.74 (dd, J = 2.0, 8.1 Hz, 1H, Ar-H), 8.18 (d, J = 1.7 Hz, 1H, Ar-H).
