[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[CH3:12].[Br:13]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4]([Br:11])[C:3]=1[CH2:12][Br:13]To a mixture of 2,6-dibromo-4-nitrotoluene (5.00 g, 16.95 mmol) in CCl4 (131 mL) was added N-bromosuccinimide (4.22 g, 23.73 mmol) and dibenzoyl peroxide (411 mg, 1.70 mmol). The mixture was evacuated and flushed with argon three times, then heated using an oil bath. At reflux azo-bis-isobutyronitrile (278 mg, 1.695 mmol) was added. The reaction was stopped after 3.75 h, cooled to rt and filtered washing with CCl4. The filtrate was concentrated under reduced pressure to give a yellow solid, which was purified using flash chromatography on Biotage 40M column, eluting with 90:10 hexanes-CH2Cl2 to yield 1,3-dibromo-2-(bromomethyl)-5-nitrobenzene. 1H NMR (500 MHz, CDCl3): δ 4.8 (s, 2H), 8.4 (s, 2H).
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