Iodine → 2-[4-(4-Iodo-3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol

Participants

Reaction Steps

A mixture of 2-[4-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol (step 1, 1.26 g, 5.8 mmol), iodine (883 mg, 3.5, mmol) and ceric ammonium nitrate (1.59 g, 2.9 mmol) was stirred in acetonitrile (58 mL) at room temperature for 1 h. Then, the solvent was evaporated under reduced pressure and the resulting residue was dissolved dichloromethane. The organic solution was washed with 5% aqueous solution sodium thiosulfate, then with brine, and finally dried (Na2SO4) and evaporated. The crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 1.54 g (78%) of the title compound as yellow solids: MS (ESI) m/z 343 [M+H]+, 1H-NMR (CDCl3) δ 7.32 (4H, s), 3.86 (2H, t, J=6.6 Hz), 2.91 (2H, t, J=6.6 Hz), 2.33 (3H, s), 2.30 (3H, s), 1.67 (1H, br.s).

Provenance & Evidence