反应详情

温度

0 °C

To 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.

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringstirred for 3 hours
3. temperatureThe reaction was cooled down to 0° C.
4. customto quench
5. customthe reaction
6. temperatureto warm to room temperature
7. washwashed with saturated aqueous sodium bicarbonate and saturated aqueous sodium thiosulfate
8. customThe organic layer was separated
9. extractionthe aqueous layer was back extracted two times with ethyl acetate
10. dry with materialThe combined organic layers were dried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe residue was purified by column chromatography on silica gel (ethyl acetate/ioshexane gradient)