Hydrogen Peroxide → 2-(3,5-Difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenyl)ethanol

HRID 705927Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 705927
[F:1][C:2]1[CH:18]=[C:17]([CH:19]=[CH2:20])[CH:16]=[C:15]([F:21])[C:3]=1[O:4][C:5]1[CH:6]=[N:7][C:8]([C:11]([F:14])([F:13])[F:12])=[N:9][CH:10]=1.B1C2CCCC1CCC2.[OH-:31].[Na+].OO>C1COCC1>[F:21][C:15]1[CH:16]=[C:17]([CH2:19][CH2:20][OH:31])[CH:18]=[C:2]([F:1])[C:3]=1[O:4][C:5]1[CH:10]=[N:9][C:8]([C:11]([F:12])([F:13])[F:14])=[N:7][CH:6]=1

Komponenten

6

Edukt 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 677743945-(2,6-Difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine

Produkt 1

HCID 677749302-(3,5-Difluoro-4-((2-(trifluoromethyl)pyrimidin-5-yl)oxy)phenyl)ethanolAusbeute 153 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the solution of 5-(2,6-difluoro-4-vinylphenoxy)-2-(trifluoromethyl)pyrimidine (1.67 g, 5.53 mmol) in dry THF (25 mL), was added 9-BBN (20 ml, 10.00 mmol) at 0° C. The mixture was stirred at room temperature overnight, and quenched with water (2 mL), followed by aq. NaOH (7 mL, 21.0 mmol), and 30% H2O2 (7 mL, 5.53 mmol). The reaction mixture was heated at 50° C. for 3 h. Then THF was removed under reduced pressure, and the residue was diluted with EA. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated and purified by flash chromatography to afford the title compound (2.7 g, 8.43 mmol, 153% yield) as a white oil. LCMS: rt=2.97 min, [M+H+]=321

Aufarbeitung

  1. customquenched with water (2 mL)
  2. temperatureThe reaction mixture was heated at 50° C. for 3 h
  3. customThen THF was removed under reduced pressure
  4. additionthe residue was diluted with EA
  5. washThe organic layer was washed with water and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-061752a51f2e4ae9b31cd1c63a10db89
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174968B2

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