Azobisisobutyronitrile → 2-(Bromomethyl)-3-nitropyridine

2,2′-azobis(isobutyronitrile) (2.7 g, 16.4 mmol) was added to a solution of 2-methyl-3-nitropyridine (12.97 g, 92.6 mmol) prepared in Step 1 and N-bromosuccinimide (23.06 g, 130 mmol) in carbon tetrachloride (100 ml) and then the reaction mixture was refluxed for 3 days. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was diluted with ethyl acetate (100 ml) and then washed with a saturated sodium bicarbonate solution and a saturated sodium thiosulfate solution. The organic layer was dried on anhydrous magnesium sulfate and then purified with silica gel column chromatography (dichloromethane/n-hexane=2/1, v/v) to give 7.5 g of the titled compound as brown oil.

1. temperaturethe reaction mixture was refluxed for 3 days
2. concentrationconcentrated under reduced pressure
3. additionThe resulting residue was diluted with ethyl acetate (100 ml)
4. washwashed with a saturated sodium bicarbonate solution
5. dry with materialThe organic layer was dried on anhydrous magnesium sulfate
6. custompurified with silica gel column chromatography (dichloromethane/n-hexane=2/1

ORD record

ord-e10716f0faa7462b9b93969b1a322a5d

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07662832B2