[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[CH3:15].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.N(C(C)(C)C#N)=NC(C)(C)C#N>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[C:6]([O:13][CH3:14])[C:5]=1[CH2:15][Br:17]To a suspension of 3-Methoxy-2-methyl-6-nitro-benzoic acid methyl ester (4.1 g, 18.2 mmol) and N-bromosuccinimide (3.89 g, 21.8 mmol) in 50 mL of CCl4 is added 2,2′-azobisisobutyronitrile (299 mg, 1.82 mmol) at room temperature. The reaction mixture is stirred at 85° C. for 21 hours and then cooled to room temperature. The reaction mixture is cooled to room temperature and then quenched by crushed ice. The mixture is extracted with ethyl acetate and washed with aqueous NaHCO3 solution followed by brine, dried over Na2SO4, filtered and evaporated in vacuo to afford the 2-Bromomethyl-3-methoxy-6-nitro-benzoic acid methyl ester (7.1 g) as orange oil. 1H-NMR (400 MHz, δ, ppm) CDCl3: 4.0 (s, 3H), 4.05 (s, 3H), 4.52 (s, 2H), 7.02 (d, 1H), 8.2 (d, 1H).
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