Methyl chloroformate → Methyl 4-bromo-2-chloronicotinate

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-2-chloro-pyridine (4.5 mL, 41 mmol) in anhydrous THF (60 mL) was added dropwise to a stirred solution of lithium diisopropylamide (1.8 M in THF, 25 mL, 45 mmol) in anhydrous THF (60 mL) at −85° C. After stirring for 30 min at −80° C., the reaction mixture was added dropwise via cannula to a stirred solution of methylchloroformate (31 mL, 400 mmol) in anhydrous THF at −80° C. After stirring for 50 min at −80° C., the reaction was quenched by the addition of concentrated aqueous NaHCO3 (90 mL), and subsequently diluted with EA (250 mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with hexane/EA 4:1) to give the title compound. MS (m/z): 252.0.1 [M+H+].

Provenance & Evidence