(3-Benzyloxy-5-trifluoromethylthien-2-yl)-carboxylic acid → 3-Benzyloxy-5-trifluoromethylthiophen

HRID 23327

Reaktionsgleichung

Reaktionsgleichung von HRID 23327
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[S:11][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Cu].N1C2C(=CC=CC=2)C=CC=1>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([F:17])([F:15])[F:16])[S:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 1

HCID 11426602(3-Benzyloxy-5-trifluoromethylthien-2-yl)-carboxylic acid

Produkt 1

HCID 111844703-Benzyloxy-5-trifluoromethylthiophenAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23978CopperKatalysatorHCID 7047QuinolineLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5F (14.5 g) and quinoline (50 ml) was treated with copper powder (4.57 g) and heated to 150° C. The reaction mixture is heated for 25 minutes at 150° C. and cooled to room temperature. The mixture was filtered and washed with water. Aqueous quinoline was acidified with 6N HCl (pH=2) and extracted with diethyl ether twice. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue was chromatographed to yield a yellow liquid (8.74 g, 71%).

Aufarbeitung

  1. temperatureThe reaction mixture is heated for 25 minutes at 150° C.
  2. temperaturecooled to room temperature
  3. filtrationThe mixture was filtered
  4. washwashed with water
  5. extractionextracted with diethyl ether twice
  6. washThe combined organic phases were washed with water
  7. customdried
  8. concentrationThe mixture was concentrated
  9. customthe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-c4f7d550f4084b819d2aa770f40142bf
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852673B2

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