2-Bromopyridine → 6'-Chloro-[2,3']bipyridinyl

Participants

Reaction Conditions

Reaction Steps

In a 300 mL inner volume flask replaced by nitrogen, tetrahydrofuran solution containing isopropylmagnesium chloride (19.5% by weight, 30.3 g, 57.5 mmol) was charged, and cooled at 10° C., and then, tetrahydrofuran solution (20 g) containing 5-bromo-2-chloropyridine (9.6 g, 50.0 mmol) was added dropwise in the range of 10 to 20° C. for 1.0 hour. After adding dropwise, the reaction mixture was stirred in the range of 10 to 20° C. for 1.5 hours, and then reaction mixture was added dropwise to the solution of tetrahydrofuran (20 g) containing 2-bromopyridine (7.9 g, 50.0 mmol) and [1,1′-bis(diphenylphosphino)propane]nickel dichloride (0.14 g, 0.25 mmol) in the range of 10 to 20° C. for 2.0 hours. After adding dropwise, the reaction mixture was stirred in the range of 10 to 20° C. for 4.0 hours. However, 6-chloro-3,2′-bipyridine could not be obtained.

Provenance & Evidence