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

Temperature

0 °C

2,3-Dichloropyridine (1.0 g, 6.8 mmol) 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, 10.2 mmol) was added dropwise to the reaction mixture under a nitrogen atmosphere 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. Brine was slowly added to the reaction mixture (20 mL) and the product extracted with TBME (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 heptane to yield the title compound as a yellow oil (0.108 g, 0.6392 mmol).

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

ORD record

ord-f4f75c4c3d714dd4a13aa88b391bad43

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102621B2