Dimethylformamide → 6-Bromo-3-pyridinecarboxaldehyde

Participants

Reaction Steps

To a suspension of 2,5-dibromopyridine (18.6 g, 78.5 mmol) in dry diethyl ether (400 mL) at −78° C. was added n-butyllithium (2.5 M in hexanes, 31.4 mL, 78.5 mmol) over a period of 20 min. After stirring 30 min at this temperature, anhydrous DMF (9.1 mL, 118 mmol) was added over a period of 5 min, and the reaction mixture was stirred for 30 min then warmed to room temperature. Saturated NH4Cl (10 mL) was added to the reaction mixture. The layers were separated, and the organic layer was dried (Na2SO4), concentrated. The crude product was purified by column chromatography (1:5 ethyl acetate/hexanes) to afford a brown solid (12.5 g, 86%); 1H NMR (300 MHz, CDCl3) δ 7.61 (dd, J=8.10, 0.60 Hz, 1 H), 7.95 (dd, J=8.10, 2.10 Hz, 1 H), 8.74 (dd, J=2.10, 0.60 Hz, 1 H), 10.02 (s, 1 H); 13C NMR (75 MHz, CDCl3) 129.2, 130.8, 137.7, 148.4, 152.6, 189.7.

Provenance & Evidence