Hydrogen Peroxide → 5-Chloro-6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-ol

Hydrogen peroxide solution (30% aq. solution, 30.2 mL, 0.26 mol) was added to a solution of 3-chloro-2-(2,2,3,3-tetrafluoropropoxy)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (Preparation 49, 81.0 g, 0.22 mol) in methanol (500 mL) at 0° C. and the reaction was allowed to warm up to room temperature for 4 hours. The reaction mixture was quenched with aqueous sodium thiosulphate (10%, 100 mL) and the methanol removed in vacuo. The resulting mixture was extracted with EtOAc (2×250 mL). The combined organics swere dried over magnesium sulfate, filtered and evaporated to yield a yellow oil, which was purified by silica gel chromatogrpahy eluting with 10% EtOAc in heptane to afford the title compound as a viscous colourless oil (46.7 g, 82%).

1. customThe reaction mixture was quenched with aqueous sodium thiosulphate (10%, 100 mL)
2. customthe methanol removed in vacuo
3. extractionThe resulting mixture was extracted with EtOAc (2×250 mL)
4. dry with materialThe combined organics swere dried over magnesium sulfate
5. filtrationfiltered
6. customevaporated
7. customto yield a yellow oil, which
8. customwas purified by silica gel chromatogrpahy
9. washeluting with 10% EtOAc in heptane

ORD record

ord-6b72bef20ffb45cc99ad59954b37316d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102621B2