4-Iodopyridine

110-86-1

15854-87-2

GENERAL METHODS: [Li(TMP)Zn(tBu)2] 1 was prepared according to literature methods in a 0.4 mmol scale solution of THF. Pyridine (0.032 mL, 0.4 mmol) was added to this solution at 0°C and the resulting light orange colored reaction mixture was allowed to stir for 2 h at room temperature. Subsequently, the reaction was quenched with I2 (508 mg, dissolved in 1 mL THF) and stirring was continued for 1 hour. A 10% Na2S2O3 solution was added until the color of the reaction mixture faded, and then the product was extracted with DCM (3 x 1 mL). The organic extracts were combined, dried with MgSO4 and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel column chromatography using EtOAc:heptane (20:80→30:70) as eluent to afford 4-iodopyridine (compound 5a) as an off-white solid (42 mg, 50% yield).1H NMR (400 MHz, CDCl3) δ ppm 7.59-7.86 (m, 2H), 8.07-8.44 (m 2H).