[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:11][C:12]1[CH:17]=[C:16]([I:18])[CH:15]=[C:14](Cl)[N:13]=1.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[CH2:3]([O:10][C:14]1[CH:15]=[C:16]([I:18])[CH:17]=[C:12]([Cl:11])[N:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1To a solution of sodium hydride (1.24 g, 31.0 mmol, 60 wt % in mineral oil) in THF (30.4 mL) at 0° C. was added benzyl alcohol (2.09 mL, 20.1 mmol) dropwise via syringe. After stirring at 0° C. for 30 mins, 2,6-dichloro-4-iodopyridine (5.00 g, 18.3 mmol) in THF (5 mL) was added dropwise via syringe. The reaction mixture was warmed to room temperature and stirred for 3 hours. The reaction was cooled down to 0° C., and saturated aqueous ammonium chloride was slowly added to quench the reaction. The reaction mixture was allowed to warm to room temperature, diluted with ethyl acetate, and washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate. The organic layer was separated and the aqueous layer was back extracted two times with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/ioshexane gradient) to give 2-(benzyloxy)-6-chloro-4-iodopyridine. LRMS (ESI) calculated for C12H10ClINO [M+H]+, 345.9; found 345.8.
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