Sodium Carbonate → (1R)-1-(3',5'-dinitrobiphenyl-4-yl)-2,2-difluoroethanol

Temperatur

85 °C

A mixture of 1-bromo-3,5-dinitrobenzene (5 g, 19.6 mmol), PdCl2(dppf)-dichloromethane adduct (0.802 g, 0.982 mmol), {4-[(1R)-2,2-difluoro-1-hydroxyethyl]phenyl}boronic acid (4.36 g, 21.6 mmol), and aqueous sodium carbonate (2 M, 29.5 mL, 58.9 mmol) in dioxane (65.6 mL) was degassed by sparging with nitrogen. The mixture was heated to 85° C. for 2 hours, and then allowed to cool to room temperature. The mixture was diluted with water, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) to give (1R)-1-(3′,5′-dinitrobiphenyl-4-yl)-2,2-difluoroethanol as an off-white solid. MS ESI calc'd. for C14H9F2N2O4[M+H−H2O]+ 307, found 307.

1. customwas degassed
2. customby sparging with nitrogen
3. temperatureto cool to room temperature
4. additionThe mixture was diluted with water
5. extractionextracted with ethyl acetate
6. washwashed with brine
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

ORD-Eintrag

ord-94b656cdf2a84dd1b49eb422c18933f2

Quelldatensatz

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09353066B2