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

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

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

ORD record

ord-6b2d5f34bc3c44b69e622cbb06ffa55d

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927550B2