[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([CH2:11][O:12][CH3:13])[CH:3]=1.CCO.O.[Cl-].[NH4+]>C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([CH2:11][O:12][CH3:13])[CH:3]=1)[NH2:8]To a solution of the product of Step 1 (470 mg, 1.910 mmol) in (EtOH/water) (8.5 mL/4.2 mL) were added iron (533 mg, 9.55 mmol) and ammonium chloride (51 mg, 0.955 mmol). The reaction was stirred at 90° C. for about 4 hours. The reaction was then allowed to come to room temperature and diluted with ethyl acetate. The solution was then filtered through Celite and organic solvent was then removed in vacuo. Flash chromatography (hexane/ethyl acetate: 70/30) was used for purification to afford 3-bromo-5-(methoxymethyl)aniline (258 mg, 1.194 mmol, 62.5% yield). MS ESI: [M+H]+ m/z=216.0.
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