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3,5-Dibromopicolinonitrile → HCID 59799017, Verbindung

HRID 2364548
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2364548
[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[Cl-].[F:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][Zn+])=[CH:15][CH:14]=1>O1CCCC1.O.C(OCC)(=O)C.Cl.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.[Pd]>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][CH:5]=[C:6]([CH2:17][C:16]2[CH:19]=[CH:20][C:13]([F:12])=[CH:14][CH:15]=2)[CH:7]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 2

HCID 123612023,5-DibromopicolinonitrileHCID 178505764HCID 178505764, Verbindung2×

Produkt 1

HCID 59799017HCID 59799017, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 313Hydrochloric AcidKatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladium
Katalysator
HCID 962WaterLösungsmittel
HCID 8028TetrahydrofuranLösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

3,5-dibromo-2-pyridinecarbonitrile (4.52g, 15.34 mmol) was dissolved in tetrahydrofuran (75 mL) and palladium tetrakis(triphenylphosphine) (0.887g, 0.767 mmol) and 4-fluorobenyl zinc chloride (46.02 mL, 0.5 M in tetrahydrofuran) were added. The mixture was heated at 85° C. for 1 hour. An additional 12.3 mL of 4-fluorobenyl zinc chloride was added and the reaction was heated 40 minutes and allowed to cool to ambient temperature. The mixture was diluted with water and ethyl acetate and several drops of 1 N hydrochloric acid were added and the reaction was extracted with ethyl acetate. The organics were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. Purification by silica gel chromatography (0-100% ethyl acetate/hexanes gradient elution) gave 3-bromo-5-[(4-fluorophenyl)methyl]-2-pyridinecarbonitrile (2.54g, 57% yield) as a pale yellow solid. 1H NMR (CDCl3) δ 8.48 (s, 1 H), 7.74 (s, 1 H), 7.15-7.11 (m, 2 H), 7.07-7.02 (m, 2 H), 4.02 (s, 2 H); MS m/z 292 (M+1).

Aufarbeitung

  1. temperaturethe reaction was heated 40 minutes
  2. temperatureto cool to ambient temperature
  3. additionwere added
  4. extractionthe reaction was extracted with ethyl acetate
  5. washThe organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customPurification
  9. washby silica gel chromatography (0-100% ethyl acetate/hexanes gradient elution)

Quellen und Nachweise

ORD-Eintrag
ord-5e30e92fbca941b8b54d2061640ccce4
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08691991B2

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