Dimethylformamide → 5-Chloropyridine-2-carboxaldehyde

Participants

Reaction Conditions

Reaction Steps

Isopropyl magnesium chloride (11.5 mL, 2 M in THF, 23 mmol) was added dropwise to a cold (−15° C.) solution of 5-chloro-2-iodo-pyridine (5 g, 20.9 mmol) in THF (35 mL). The mixture was stirred for 1 h at −15° C. DMF (2.3 g, 31.3 mmol) was added dropwise keeping the internal temperature below 0° C. The mixture was allowed to warm to rt, stirred for 1 h, cooled to 0° C., quenched by addition of a saturated aqueous solution of ammonium chloride, and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by silica gel column chromatography (hexane/EtOAc, 95:5) to provide 1.1 g of the title compound. tR: 0.39 min (LC-MS 2); ESI-MS: 142 [M+H]+ (LC-MS 2); Rf=0.22 (hexane/EtOAc, 4:1).

Provenance & Evidence