5-((trimethylsilyl)methyl)-2,2'-bipyridine (1.16 g, 4.5 mmol), hexachloroethane (4.06 g, 9.0 mmol) and caesium fluoride (1.46 g, 9.0 mmol) were suspended in dry acetonitrile (75 ml) and heated to 60˚C for 4 H under an atmosphere of dinitrogen. The reaction mixture was cooled to 25˚C, water (100 ml) was added and the product was extracted in to ethyl acetate (3 x 150 ml). The organic fractions were combined, washed with brine, dried over sodium sulphate, filtered and solvents were removed under reduced pressure. The product was purified by sublimation of any residual hexachloroethane at 60˚C under vacuum to leave the desired product as a beige solid. Yield = 0.84 g, 84 %.

¹H NMR (300 MHz, 298 K, CDCl₃) δ_H ppm 8.71-8.66 (2H, m, Py), 8.45-8.38 (2H, m, Py), 7.89-7.79 (2H, m, Py), 7.32 (1H, ddd, ³J_HH = 7.4 Hz ³J_HH = 4.9 Hz ⁴J_HH = 1.1, Py), 4.65 (2H, s, C­H₂).

¹³C{¹H} NMR (75 MHz, 298K, CDCl₃) δ_C ppm 156.2 (py), 155.6 (py), 149.3 (py), 149.0 (py), 137.3 (py), 137.0 (py), 133.2 (py), 124.0 (py), 121.3 (py), 121.0 (py), 43.2 (CH₂).

MS (ESI) m/z 205.0 [M+H]⁺.

IR cm^-1: 3053 (w), 3008 (w), 2969 (w), 1598 (m), 1587 (m), 1573 (m), 1557 (m), 1493 (w), 1458 (m), 1436 (m), 1392 (m), 1263 (m), 1219 (w), 1196 (w), 1149 (w), 1128 (w), 1090 (w), 1062 (w), 1041 (w), 1028 (m), 993 (w), 935 (w), 904 (s), 857 (w), 834 (m).

Elemental Analysis found (Calculated for C₁₁H₉N₂Cl) % C 64.56 (64.56), H 4.32 (4.43), N 13.58 (13.68).