1,2-Dimethoxyethane → 3-bromo-5-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyridine

HRID 2388026Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2388026
[Br:1][C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[CH2:13]([O:15]/[CH:16]=[CH:17]/B1OC(C)(C)C(C)(C)O1)[CH3:14].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][CH:5]=[C:6](/[CH:14]=[CH:13]/[O:15][CH2:16][CH3:17])[CH:7]=1

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 110449423,5-Dibromo-2-(trifluoromethyl)pyridineHCID 219739081-Ethoxyethene-2-boronic acid pinacol ester

Produkt 1

HCID 594049863-bromo-5-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyridineAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 3,5-dibromo-2-(trifluoromethyl)pyridine (1.11 g, 3.65 mmol) in water (9 mL) were added 2-[(E)-2-ethoxyvinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.72 g, 3.65 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.42 g, 0.36 mmol), 1,2-dimethoxyethane (16.7 mL), and sodium carbonate (1.16 g, 11.0 mmol). The resulting mixture was allowed to stir overnight at 60° C. After the reaction was allowed to cool to rt, EtOAc (50 mL) was added. The organic solution was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-bromo-5-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyridine (0.41 g, 38%).

Aufarbeitung

  1. temperatureto cool to rt
  2. customThe organic solution was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3e05e4ed91d640f6b97f54a238301d69
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08268992B2

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