反应详情

温度

60 °C

To a 500 mL RBF was added neopentylmagnesium chloride, 111.0M in ether (28.0 ml, 28 mmol) and an ice bath. After cooling, zinc(II) chloride, 0.5M in THF (56.0 ml, 28 mmol) was added dropwise. The cooling bath was removed and after stirring for 45 minutes, Reactant 1 (0.26 g, 0.32 mmol) was added followed by 2,6-difluoro-3-iodopyridine (2.74 g, 8.0 mmol) in THF (10 mL), which was added dropwise. The yellow solution was then heated to 60° C. After stirring overnight the reaction was allowed to cool and sat'd. NH4Cl was added cautiously. The reaction mixture was partitioned between EtOAc/Water. The aqueous layer was extracted with EtOAc (50 mL) and the combined organic layers washed with brine and concentrated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with 1% EtOAc in hexane, to provide 2,6-difluoro-3-neopentylpyridine as a colorless oil. MS m/z: 186 (M+1).

1. temperatureAfter cooling
2. customThe cooling bath was removed
3. additionwas added dropwise
4. stirringAfter stirring overnight the reaction
5. temperatureto cool
6. customThe reaction mixture was partitioned between EtOAc/Water
7. extractionThe aqueous layer was extracted with EtOAc (50 mL)
8. washthe combined organic layers washed with brine
9. concentrationconcentrated in vacuo
10. customchromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
11. washeluting with 1% EtOAc in hexane