2-Chloro-3-nitropyridine → 2-Mesityl-3-nitropyridine

HRID 584806

Reaktionsgleichung

Reaktionsgleichung von HRID 584806
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COC(OC)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>[C:11]1([CH3:23])[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[C:12]=1[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 3

HCID 796132-Chloro-3-nitropyridineHCID 17749109Barium hydroxide, octahydrateHCID 22237855Mesitylboric acid

Produkt 1

HCID 222494912-Mesityl-3-nitropyridineAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 107951,1-DimethoxyethaneLösungsmittel

Versuchsvorschrift

A solution of 2-chloro-3-nitropyridine (5.0 g, 31.5 mmol), mesitylboric acid (5.65 g, 34.7 mmol), Pd(PPh3)4 (1.82 g, 1.58 mmol) and barium hydroxide octahydrate (14.9 g, 47.3 mmol) in 2,2-dimethoxyethane (150 mL) and water (25 mL) was heated under reflux for one day. The mixture was filtered through Celite, and the filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatogrpahy (10% ethyl acetate/hexane), to give the title compound (5.99 g) as pale yellow oil.

Aufarbeitung

  1. temperatureunder reflux for one day
  2. filtrationThe mixture was filtered through Celite
  3. additionthe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatogrpahy (10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-b485dba6324740099c6abd966643b6bc
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927221B2

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