Diethyl Ether → 2-tert-Butyl-3-chloropyridine

Temperature

0 °C

2,3-Dichloropyridine (1.0 g, 0.0068 mol) and copper iodide (0.065 g, 0.341 mmol) were dissolved in THF (6 mL). The mixture was degassed three times then cooled to 0° C. with an ice bath. Then tert-butyl(chloro)magnesium in diethylether (5.10 mL, 0.0102 mol) was added drop wise to the reaction mixture under nitrogen keeping the temperature at 0° C. with an ice bath. When the addition was complete, it was left to warm up to room temperature for 16 hours. A saturated aqueous solution of sodium chloride was slowly added to the reaction mixture (20 mL). The product was then extracted with tert-butyl methyl ether (20 mL). The organic layer was then dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 0 to 5% EtOAc in heptanes to yield the title compound as a yellow oil (0.108 g, 9% yield).

1. customThe mixture was degassed three times
2. additionWhen the addition
3. waitit was left
4. temperatureto warm up to room temperature for 16 hours
5. extractionThe product was then extracted with tert-butyl methyl ether (20 mL)
6. dry with materialThe organic layer was then dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting crude was purified by silica gel chromatography
10. washeluting with 0 to 5% EtOAc in heptanes

ORD record

ord-3a9461ddd06f413596eaa6989600f111

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592629B2