2,5-Dibromopyridine → 5-Bromopyridine-2-carbonitrile

2,5-Dibromopyridine (20.0 g, 84.4 mmol) was dissolved in dimethylformamide (422 mL). To the stirred solution was added copper(I) cyanide. After refluxing for 5 h, the mixture was cooled to room temperature and stored overnight. The reaction mixture was diluted with ethyl acetate (1200 mL) and filtered through a Buchner funnel containing sand, Celite, and silica gel layers. The filtrate was concentrated to a volume of 400 mL. This organic liquid was diluted with water (300 mL) and the resulting liquid was extracted with ethyl acetate (2×200 mL). The organic extracts were combined, washed with water (2×300 mL) and brine (1×250 mL), and dried over magnesium sulfate. After concentration, the product was purified via silica gel chromatography (50:50 ethyl acetate/CH2Cl2) to afford the title compound (9.79 g).

1. temperatureAfter refluxing for 5 h
2. filtrationfiltered through a Buchner funnel
3. additioncontaining sand, Celite, and silica gel layers
4. concentrationThe filtrate was concentrated to a volume of 400 mL
5. additionThis organic liquid was diluted with water (300 mL)
6. extractionthe resulting liquid was extracted with ethyl acetate (2×200 mL)
7. washwashed with water (2×300 mL) and brine (1×250 mL)
8. dry with materialdried over magnesium sulfate
9. concentrationAfter concentration
10. customthe product was purified via silica gel chromatography (50:50 ethyl acetate/CH2Cl2)

ORD record

ord-2c2e001a030c4e13b0ab22bb9d9a7f9c

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06667311B2