2,6-Dichloropyridine → HCID 57700380, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dichlorophenylacetic acid (4.1 g) in THF (100 mL) was added n-butyl lithium (1.4 M, in hexanes, 30 mL) slowly at 0° C. The resulting mixture was stirred at 0° C. for ½ hr and then cooled to −78° C. To this solution was added 2,6-dichloropyridine (2.96 g) at −78° C. then warmed to room temperature and stirred for approximately 1-3 hours. The mixture was re-cooled to −78° C. and oxalyl chloride (1.9 mL) was added. The resulting mixture was warmed to room temperature and stirred for 1 hr. The solution was re-cooled to −78° C. and ethynylmagnesium bromide (0.5 N, 44 mL) was added. The mixture was slowly warmed to room temperature. The reaction was quenched with 0.1 N HCl, and extracted with ether. The organic layer was separated, washed with brine solution, dried over magnesium sulfate, filtered, and evaporated. The residue was purified by silica gel (hexanes/methylene chloride=3/1) to give desired compound as a yellowish solid (0.59 g).

Provenance & Evidence