Azobisisobutyronitrile → HCID 89996178, compound

Temperature

80 °C

To a stirred solution of 5-bromo-2-iodo-3-methyl-pyridine (22.5 g, 75.5 mmol, 1 eq) in 1,2-dichloroethane (200 mL) was added NBS (20.16 g, 113.255 mmol, 1.5 eq) followed by addition of AIBN (4.96 g, 30.2 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 (150 mL), extracted with DCM (2×150 mL). Combined organic phase was washed with brine (200 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to get dark brownish semi solid (25 g, crude). Crude of title compound was used as such for next reaction. 1H NMR (400 MHz, CDCl3) δ: (Mixture of starting with product): 4.45 (s, 2H), 7.81 (d, J=2.36 Hz, 1H), 8.31 (d, J=2.36 Hz, 1H). LC-MS (m/z): 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 (150 mL)
6. extractionextracted with DCM (2×150 mL)
7. washCombined organic phase was washed with brine (200 mL)
8. dry with materialdried over anhydrous Na2SO4
9. concentrationconcentrated under reduced pressure
10. customto get dark brownish semi solid (25 g, crude)

ORD record

ord-eee90533dfba4209898b51289dc77eae

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09131697B2