2,6-Dibromopyridine → 2-(6-Bromopyridin-2-yl)benzonitrile

HRID 1796041

Reaktionsgleichung

Reaktionsgleichung von HRID 1796041
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N:3]=1.CC1(C)C(C)(C)OB([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:4]1[N:3]=[C:2]([C:17]2[CH:24]=[CH:23][CH:22]=[CH:21][C:18]=2[C:19]#[N:20])[CH:7]=[CH:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 122742,6-DibromopyridineHCID 62657Potassium Phosphate, TribasicHCID 35702292-(2-Cyanophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 221807852-(6-Bromopyridin-2-yl)benzonitrileAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2,6-Dibromopyridine (0.47 g, 2.0 mmol), 2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile (0.69 g, 3.0 mmol) and potassium phosphate (0.85 g, 4.0 mmol) were dissolved in N,N-dimethylformamide (10 ml) and degassed with nitrogen for 15 min. Tetrakis(triphenylphosphine)palladium(0) (70 mg, 0.06 mmol) was added then the mixture heated at 80° C. for 16 h. The mixture was allowed to cool to ambient temperature, diluted with water (200 ml) and extracted into ethyl acetate (2×150 ml). The combined organics were washed with brine (200 ml), dried over anhydrous sodium sulfate and evaporated to give a yellow oil. Purification by flash column chromatography on silica eluting with isohexane on a gradient of ethyl acetate (10-30%) gave 2-(6-bromopyridin-2-yl)benzonitrile (0.518 g, 100%) as a waxy solid: δH (360 MHz, CDCl3) 7.53-7.57 (2H, m), 7.68-7.72 (2H, m), 7.80 (1H, d, J 8), 7.86-7.90 (1H, m).

Aufarbeitung

  1. customdegassed with nitrogen for 15 min
  2. temperatureto cool to ambient temperature
  3. extractionextracted into ethyl acetate (2×150 ml)
  4. washThe combined organics were washed with brine (200 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated
  7. customto give a yellow oil
  8. customPurification by flash column chromatography on silica eluting with isohexane on a gradient of ethyl acetate (10-30%)

Quellen und Nachweise

ORD-Eintrag
ord-97d78873c8b54da3b5a4dc55871be600
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07030128B2

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