Azobisisobutyronitrile → HCID 89996178, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence