Dimethylformamide → 6-Bromo-3-pyridinecarboxaldehyde

Temperature

-78 °C

2,5-Dibromopyridine 9.48 g (40 mmol) was dissolved in 60 mL of THF and 150 mL of anhydrous ether. After the solution was cooled to −78° C., 16 mL of n-butyllithium (2.5 M, 40 mmol) was slowly dropped through a syringe in 30 min. After being stirred at −78° C. for 30 minutes, N,N-dimethylformamide (3.5 g, 48 mmol) was added. The reaction mixture was warmed up to room temperature during two hours and then quenched by addition of 10 mL of water. The mixture was extracted twice using EtOAc. The combined extracts were dried and concentrated. After flash column using 30-40% EtOAc in hexane, 2.80 g of white solid was obtained (28% yield), MS: 186.0, 188.0 (M++1).

1. temperatureThe reaction mixture was warmed up to room temperature during two hours
2. customquenched by addition of 10 mL of water
3. extractionThe mixture was extracted twice using EtOAc
4. customThe combined extracts were dried
5. concentrationconcentrated

ORD record

ord-a9850c21b721423bb01556b04ba8cb63

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362003B2