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

To a solution of 1-(2-bromo-pyridin-4-yl)-propan-1-ol (2.20 g 10.2 mmol) in dichloromethane (55 mL) was added Dess-Martin periodinane (5.6 g, 13 mmol). After 30 hours, and was diluted with saturated aqueous sodium carbonate (40 mL) and partially concentrated to remove the dichloromethane. The crude material was filtered through diatomaceous earth and washed with EtOAc (100 mL). The aqueous layer was separated and extracted with EtOAc (40 mL). The combined organic layers were washed with saturated aqueous sodium carbonate (40 mL) and brine (40 mL). The material was dried over magnesium sulfate, filtered and concentrated to afford 1-(2-bromo-pyridin-4-yl)-propan-1-one as a clear oil which was used without further purification.

1. concentrationpartially concentrated
2. customto remove the dichloromethane
3. filtrationThe crude material was filtered through diatomaceous earth
4. washwashed with EtOAc (100 mL)
5. customThe aqueous layer was separated
6. extractionextracted with EtOAc (40 mL)
7. washThe combined organic layers were washed with saturated aqueous sodium carbonate (40 mL) and brine (40 mL)
8. dry with materialThe material was dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-1e0b749a9b964dad84efb2cb82634aaa

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163918B2