Hydrochloric Acid → 6-Bromo-3-pyridinecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2,5-dibromopyridine (2.00 g, 8.44 mmol) in dry diethyl ether (25 mL) was added n-BuLi (3.55 mL, 8.87 mmol, 2.5 M solution in hexane) at −80° C. under a nitrogen atmosphere. After stirring for 1 h at −80° C. dry DMF (0.68 mg, 9.28 mmol) was added. After stirring for an additional hour at −80° C. the reaction mixture was allowed to warm to 0° C. and HCl (18.0 mL, 1 M) was added. After stirring for 15 minutes the phases were separated and aqueous layer was extracted twice with diethyl ether. The combined organic layers were washed with water (50 mL), brine (50 mL) and dried over MgSO4. The organic phase was concentrated under reduced pressure and the crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (8:1) as eluent. White solid. Yield: 1.03 g, 66%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=7.67-7.71 ppm (m, 1H), 8.02 (dd, J=8.2, 2.5 Hz, 1H), 8.84 (dd, J=2.5, 0.6 Hz, 1H), 10.10 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=129.0, 130.6, 137.5, 148.3, 152.5, 189.4; MS (ESI): m/z=187.19 [M+H]+.

Provenance & Evidence