Triacetoxyperiodinane → HCID 79018099, compound

Participants

Reaction Steps

To a stirring solution of (5-bromo-2-fluorophenyl)(pyridin-3-yl)methanol (3.75 g, 13.3 mmol) in DCM (50 mL) was added Dess-Martin periodinane (6.21 g, 14.6 mmol) portion-wise over several minutes. The reaction was then quenched with saturated 1:1 Na2S2O3/NaHCO3 solution (140 mL) and stirred until gas evolution ceased. The aqueous layer was extracted with DCM, dried over MgSO4, and purified by column chromatography (gradient 0 to 30% EtOAc in hexanes) to give the product. 1H NMR (400 MHz, CDCl3) δ 8.98 (s, 1H), 8.83 (dd, J=4.9, 1.7 Hz, 1H), 8.14 (dd, J=7.9, 0.6 Hz, 1H), 7.73 (dd, J=6.0, 2.5 Hz, 1H), 7.68 (ddd, J=8.7, 4.5, 2.6 Hz, 1H), 7.47 (dd, J=8.0, 4.9 Hz, 1H), 7.09 (t, J=9.0 Hz, 1H).

Provenance & Evidence