Dimethylformamide → 6-Bromopyridine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2.5 M n-butyllithium in hexane (8.6 mL, 21.5 mmol) under N2, cooled to −78° C., was added dropwise a solution of 2,6-dibromopyridine (5.10 g, 21.5 mmol) in dry THF (30 mL) at such a rate that the internal temperature was below −70° C. After complete addition, the reaction mixture was stirred at −78° C. for 15 min, and then treated with anhydrous DMF (2.6 mL, 33.3 mmol). After 15 min, the reaction mixture was treated successively with acetic acid (1.36 mL) and water (21.5 mL) and then warmed to RT. The reaction mixture was poured into ethyl acetate (75 mL). The phases were separated. The aqueous phase was extracted with ethyl acetate (25 mL). The combined organic phases were washed with brine (35 mL), dried (MgSO4), filtered and concentrated to afford 3.33 g (18.0 mmol, 84%) of the desired product as a white solid.

Provenance & Evidence