Triacetoxyperiodinane → 2-Bromo-5-ethoxy-4-methylbenzaldehyde

To a solution of (2-bromo-5-ethoxy-4-methylphenyl)methanol (2.30 g, 9.38 mmol) in DCM (40 mL) was added Dess-Martin periodinane (5.97 g, 14.08 mmol). The resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was diluted with ether and was then concentrated. The residue was taken up in ether and was washed with of a mixture of 10% aqueous Na2S2O3 and saturated aqueous NaHCO3 (1/1), water and brine. The aqueous washings were back-extracted with ether and the organic layer was washed with water and brine. The combined organic layers were dried over Na2SO4 and concentrated. The residue was purified on a silica gel column eluting with 5 to 10% EtOAc in hexanes to afford the title intermediate as a white solid

1. concentrationwas then concentrated
2. washwas washed with of a mixture of 10% aqueous Na2S2O3 and saturated aqueous NaHCO3 (1/1), water and brine
3. extractionThe aqueous washings were back-extracted with ether
4. washthe organic layer was washed with water and brine
5. dry with materialThe combined organic layers were dried over Na2SO4
6. concentrationconcentrated
7. customThe residue was purified on a silica gel column
8. washeluting with 5 to 10% EtOAc in hexanes

ORD record

ord-2758611299f042d993fbf13bcc3b7b63

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2