2,2'-Bipyridine → HCID 90414371, compound

Participants

Reaction Conditions

Reaction Steps

1-Bromo-2-(2-bromo-1,1,2,2-tetrafluoroethoxy)-3-fluorobenzene (14 g, 38 mmol), copper powder (12.2 g, 192 mmol) and 2,2′-bipyridine (610 mg, 3.9 mmol) were combined in dry DMSO (55 mL) and heated to 150° C. for 1.5 h. Vacuum (ca 20 mm) was applied to the reactor and distillate was taken overhead until the pot temperature reached 100° C. The distillate containing the product and DMSO was diluted with 1:1 diethyl ether-pentane (30 mL) and washed (3×5 mL) with water, dried, and distilled at 1 atmosphere (atm) through a 200 mm Vigreux column to remove the bulk of the solvents. Vacuum (ca 20 mmHg) was applied and the fraction boiling at 60-65° C. was collected to afford the title compound as a clear liquid (5.1 g, 64%): 1H NMR (400 MHz, CDCl3) δ 7.40-7.31 (m, 2H), 7.25-7.17 (m, 1H); EIMS m/z 210.

Provenance & Evidence