Bromine → 4-(4-bromo-1H-pyrazol-1-yl)pyridine

HRID 2274761

Reaktionsgleichung

Reaktionsgleichung von HRID 2274761
[N:1]1([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.[Br:12]Br>C(O)(=O)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>[Br:12][C:4]1[CH:3]=[N:2][N:1]([C:6]2[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=2)[CH:5]=1

Komponenten

5

Edukt 2

HCID 24408BromineHCID 200417044-(1H-Pyrazol-1-yl)pyridine2×

Produkt 1

HCID 545954894-(4-bromo-1H-pyrazol-1-yl)pyridineAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×HCID 24477Sodium ThiosulfateLösungsmittel

Versuchsvorschrift

To a solution of 4-(1H-pyrazol-1-yl)pyridine (Intermediate 7; 1.1 g; 7.5 mmol) in acetic acid (10 mL) was added a solution of bromine (6 mL) in acetic acid (10 mL) dropwise. The reaction mixture was stirred for 4 hours, diluted with saturated aqueous Na2S2O3 (20 mL), and extracted with DCM (10 mL×3). The combined organic layers were washed with saturated aqueous NaHCO3 (20 mL), water (20 mL), brine (20 mL), dried over anhydrous Na2SO4, filtered, and concentrated to afford 936 mg (55%) of the title compound as a pink solid.

Aufarbeitung

  1. extractionextracted with DCM (10 mL×3)
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3 (20 mL), water (20 mL), brine (20 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-17a3d2aa27e4443195c3eaf9e5d7dde5
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09126984B2

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