Dimethylformamide → 5-Bromo-3-pyridinecarboxaldehyde

In diethyl ether (42.0 mL) was dissolved 3,5-dibromopyridine (1.00 g, 4.22 mmol). n-Butyllithium (2.76 mol/L solution in n-hexane, 1.61 mL, 4.43 mmol) was added dropwise at −78° C., and the mixture was stirred at the same temperature for 30 minutes. Further, DMF (0.98 mL, 12.7 mmol) was added and the mixture was stirred for 3 hours allowing the temperature to rise slowly to room temperature. A saturated aqueous ammonium chloride solution and water were added to the reaction mixture. Extraction with ethyl acetate, washing with saturated brine and drying over anhydrous sodium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3) to give 5-bromonicotinaldehyde (314 mg, 40%).

1. stirringthe mixture was stirred for 3 hours
2. customto rise slowly to room temperature
3. extractionExtraction with ethyl acetate
4. washwashing with saturated brine
5. dry with materialdrying over anhydrous sodium sulfate
6. filtrationAfter filtration
7. customthe solvent in the filtrate was evaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=7/3)

ORD record

ord-f6560dfcd40c443cb1469fa196c28a3d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150569B2