Toluene → 2-(5-Trifluoromethylpyridine-2-yl)benzofuran

HRID 984754

Reaktionsgleichung

Reaktionsgleichung von HRID 984754
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[O:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[CH:14]=[C:13]1B(O)O.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O.C(OCC)(=O)C.C(O)C>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([C:13]2[O:12][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH:14]=2)=[N:3][CH:4]=1

Komponenten

9

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 2776266Benzo[b]furan-2-boronic acid

Produkt 1

HCID 207673362-(5-Trifluoromethylpyridine-2-yl)benzofuranAusbeute 17,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In a 100 ml-three-necked flask, 2.80 g (15.4 mM) of 2-chloro-5-trifluoromethylpyridine, 2.50 g (15.4 mM) of 2-benzofuranylboronic acid, 14 ml of toluene, 7 ml of ethanol and 14 ml of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.55 g (0.48 mM) of tetrakis(triphenylphosphine)palladium (0) was added thereto. Thereafter, reflux under stirring for 4 hours was performed under nitrogen stream. After the reaction, the reaction mixture was cooled on an ice bath and stirred at room temperature after addition of ethyl acetate and saturated saline water. The organic layer was washed with water and dried with anhydrous magnesium sulfate, and the solvent was removed under reduced pressure to obtain a residue. The residue was purified by alumina column chromatography (eluent: toluene) and recrystallized from methanol to obtain 0.72 g of 2-(5-trifluoromethylpyridine-2-yl)benzofuran (Yield: 17.7%).

Aufarbeitung

  1. additionwas added
  2. temperatureThereafter, reflux
  3. customAfter the reaction
  4. temperaturethe reaction mixture was cooled on an ice bath
  5. stirringstirred at room temperature
  6. washThe organic layer was washed with water
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customto obtain a residue
  10. customThe residue was purified by alumina column chromatography (eluent: toluene)
  11. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-b4e18f052c4a4a7d9bdc639c55b5c39d
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869694B2

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