[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9]O)[CH:6]=[CH:5][N:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:31]>C(Cl)Cl>[Br:31][CH2:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([O:2][CH3:1])[CH:8]=1To a 100-mL round-bottomed flask was added (2-methoxy-4-pyridinyl)methanol (1.52 g, 10.92 mmol), triphenylphosphine (3.15 g, 12.02 mmol, Aldrich, St. Louis, Mo.), and carbon tetrabromide (1.165 mL, 12.02 mmol, Aldrich, St. Louis, Mo.) in DCM (20 mL). The reaction mixture was stirred at 0° C. for 2 h. The solvent was removed in vacuo and the residue was purified by silica gel chromatography, eluting with 20% EtOAc/hexanes to give 4-(bromomethyl)-2-methoxypyridine (1.98 g) as a colorless oil.
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