1,2-Dimethoxyethane → 5-Nitro-2-phenylpyridine

HRID 400576

Reaktionsgleichung

Reaktionsgleichung von HRID 400576
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.COCCOC.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C.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>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

8

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 783082-Chloro-5-nitropyridine

Produkt 1

HCID 27628735-Nitro-2-phenylpyridineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A mixture of Pd(PPh3)4 (354 mg, 1.58 mmol), 2-chloro-5-nitropyridine (5.00 g, 31.5 mmol), and phenylboronic acid (4.61 g, 37.8 mmol) was degassed and filled with nitrogen gas three times. The mixture was treated with 40 mL of DME and aqueous 2 M potassium carbonate (80.0 mmol) solution and heated to reflux. After 4 hours, the reaction mixture was cooled to room temperature and diluted with 100 mL of ethyl acetate and 50 mL of water. The phases were separated and the aqueous layer was extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with 100 mL of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. Chromatography on SiO2 (0% to 50% ethyl acetate in hexanes, gradient) give 4.60 g of 5-nitro-2-phenylpyridine (73% yield).

Aufarbeitung

  1. customwas degassed
  2. additionfilled with nitrogen gas three times
  3. temperatureheated to reflux
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with three 100 mL portions of ethyl acetate
  6. washThe combined organic layers were washed with 100 mL of brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0d2fc83538a94d86a84a025cffae5eef
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741897B2

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