Triacetoxyperiodinane → 2-Bromo-5-chloro-4-(4-ethylbenzyl)benzaldehyde

Participants

Reaction Steps

To a cooled solution (−5° C.) of (2-bromo-5-chloro-4-(4-ethylbenzyl)phenyl)methanol (9.7 g, 29.4 mmol) in dry dichloromethane (100 mL), was added dropwise a solution of Dess-Martin reagent (18.7 g, 44 mmol) in 100 mL of dry dichloromethane. After it was stirred at room temperature for 2 h, TLC showed the reaction was complete. The reaction was quenched by addition of 10 mL of 1 M NaOH. The organic layer was washed 1× with NaHSO3, 2× with NaHCO3, 3× with brine, dried over anhydrous Na2SO4. Concentration under reduced pressure provided the pure product as a white solid. Yield: 9.3 g (96%). 1H NMR (CDCl3, 300 MHz) δ 10.24 (s, 1H), 7.91 (s, 1H), 7.40 (s, 1H), 7.18 (s, 1H), 7.15 (s, 1H), 7.11 (s, 1H), 7.09 (s, 1H), 4.08 (s, 2H), 4.02 (s, 2H), 2.63 (q, J=7.8 Hz, 2H), 1.23 (t, J=7.8 Hz, 3H).

Provenance & Evidence