Acetic Acid → (1-phenyl-1H-pyrazol-5-yl)boronic acid

HRID 333721

Reaktionsgleichung

Reaktionsgleichung von HRID 333721
[C:1]1([N:7]2[CH:11]=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[B:17](OC(C)C)([O:22]C(C)C)[O:18]C(C)C.C(O)(=O)C>O1CCCC1>[C:1]1([N:7]2[C:11]([B:17]([OH:22])[OH:18])=[CH:10][CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 21531Triisopropyl borateHCID 707691-PhenylpyrazoleHCID 178418339Butyllithium

Produkt 1

HCID 59436217(1-phenyl-1H-pyrazol-5-yl)boronic acidAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-phenyl-1H-pyrazole (20.0 g) in tetrahydrofuran (700 mL) was added dropwise n-butyllithium (2.5M hexane solution, 58.3 mL) under a nitrogen atmosphere at −78° C., and the mixture was stirred at the same temperature for min. To the reaction mixture was added triisopropyl borate (52.2 g) at −78° C., and the mixture was stirred at the same temperature for 1 hr. The mixture was gradually warmed to room temperature, and stirred at room temperature for 20 hr. To the reaction mixture was added acetic acid (20 mL) to adjust to pH 5, and the mixture was concentrated to give the title compound (25.0 g).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. stirringstirred at room temperature for 20 hr
  3. concentrationthe mixture was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-0ce174f833cc450e97e671a0493ec689
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883788B2

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