Azobisisobutyronitrile → HCID 89996156, compound

Temperature

80 °C

To a stirred solution of 6-chloro-3-iodo-2-methyl-pyridine (20 g, 79 mmol, 1 eq) in 1,2-dichloroethane (200 mL) was added NBS (21.1 g, 118.6 mmol, 1.5 eq) followed by addition of AIBN (5.2 g, 31.6 mmol, 0.4 eq) at room temperature in dark. Resulting reaction mixture was heated at 80° C. for 16 hours. After maximum consumption of starting material, reaction mixture was cooled to room temperature and quenched with water (50 mL), extracted with DCM (3×50 mL). Combined organic phase was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to get dark brown semi solid (20 g, crude). Crude of title compound was used as such for next reaction. 1H NMR not clean. LC-MS: No ionization.

1. customResulting
2. customreaction mixture
3. customAfter maximum consumption of starting material, reaction mixture
4. temperaturewas cooled to room temperature
5. customquenched with water (50 mL)
6. extractionextracted with DCM (3×50 mL)
7. washCombined organic phase was washed with brine (50 mL)
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated under reduced pressure
10. customto get dark brown semi solid (20 g, crude)

ORD record

ord-2bf8c7ac00fd437e9b1e663013b2c937

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09131697B2