Triacetoxyperiodinane → 3-Bromo-2-methylbenzaldehyde

Participants

Reaction Steps

Step 1 A mixture of (3-bromo-2-methylphenyl)methanol (prepared according to the procedures reported in US Pat. Appl. 2006/0173183, 500 mg, 2.49 mmol) in THF (20 mL) was stirred at rt and treated with 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane, 1.58 g, 3.73 mmol). After 2 h, the mixture was diluted with ether (ca. 100 mL) and washed with 5% aqueous sodium bisulfite, NaHCO3 (aq) and brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 55:45 hexane-EtOAc) to provide 3-bromo-2-methylbenzaldehyde as a colorless oil (343 mg, 70%). 1H NMR (400 MHz, chloroform-d) δ 10.26 (1 H, s), 7.78 (2 H, ddd, J=9.7, 8.0, 1.2 Hz), 7.20-7.27 (1 H, m), 2.75 (3 H, s).

Provenance & Evidence