Triacetoxyperiodinane → 1-(2-Bromopyridin-4-yl)ethan-1-one

To a chilled (ice water bath) solution of 1-(2-bromo-pyridin-4-yl)-ethanol (27.5 g, 132 mmol) in dichloromethane (200 mL) was added Dess-Martin periodinane (56.0 g, 132 mmol). The cold bath was then removed and the mixture was stirred at room temperature. After 2 hours, the mixture was diluted with saturated sodium carbonate (100 mL) and partially concentrated to remove the dichloromethane. The crude material was filtered through diatomaceous earth and washed with EtOAc (200 mL). The aqueous layer was separated and extracted with EtOAc (100 mL). The combined organic layers were washed with saturated aqueous sodium carbonate (100 mL), brine (100 mL), dried over magnesium sulfate, filtered and concentrated. The crude material was purified by silica gel chromatography eluting with a gradient of 5-30% EtOAc in hexanes to afford 1-(2-bromo-pyridin-4-yl)-ethanone as white needles.

1. customThe cold bath was then removed
2. additionthe mixture was diluted with saturated sodium carbonate (100 mL)
3. concentrationpartially concentrated
4. customto remove the dichloromethane
5. filtrationThe crude material was filtered through diatomaceous earth
6. washwashed with EtOAc (200 mL)
7. customThe aqueous layer was separated
8. extractionextracted with EtOAc (100 mL)
9. washThe combined organic layers were washed with saturated aqueous sodium carbonate (100 mL), brine (100 mL)
10. dry with materialdried over magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude material was purified by silica gel chromatography
14. washeluting with a gradient of 5-30% EtOAc in hexanes

ORD record

ord-12be772ad17e4e388e09906d8c9a7fd5

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063065B2