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

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence