Water → 6-Bromo-3-pyridinecarboxaldehyde

To a solution of 2,5-dibromopyridine (2.37 g, 10.0 mmol) in tetrahydrofuran (15 mL) was added isopropylmagnesium chloride (2 mol/L in tetrahydrofuran; 5.0 mL, 10 mmol) under nitrogen atmosphere, and the mixture was stirred at room temperature for 1 h. Dimethylformamide (1.6 mL, 20 mmol) was added, and the mixture was stirred for additional 15 min. Water was added, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (2:1 hexane/ethyl acetate) to afford 2-bromo-5-pyridinecarboxaldehyde (1.23 g, 66%).

1. stirringthe mixture was stirred for additional 15 min
2. extractionthe mixture was extracted with ethyl acetate twice
3. washThe organic layer was washed with brine
4. dry with materialdried on anhydrous sodium sulfate
5. customThe solvent was evaporated under reduced pressure
6. customthe residue was purified by silica gel column chromatography (2:1 hexane/ethyl acetate)

ORD record

ord-1152158c7132425685412e5dbaf20c81

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06452014B1