Toluene → [3-(4-Trifluoromethylphenyl)phenyl]cyclopentyl sulfide

HRID 25284

Reaktionsgleichung

Reaktionsgleichung von HRID 25284
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[CH:14]1([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22](Br)[CH:21]=2)[CH2:18][CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(O)C>[CH:14]1([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:6]3[CH:7]=[CH:8][C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=3)[CH:21]=2)[CH2:15][CH2:16][CH2:17][CH2:18]1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 221708791-Bromo-3-(cyclopentylthio)benzene

Produkt 1

HCID 17808972[3-(4-Trifluoromethylphenyl)phenyl]cyclopentyl sulfideAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

1.0 g (5.2 mol) of 4-trifluoromethylphenyl boronic acid, 1.4 g (5.4 mmol) of 3-bromophenyl cyclopentyl sulfide, 1.6 g (15.0 mmol) of sodium carbonate and 0.8 g (0.7 mmol) of tetrakis(triphenylphosphine) palladium were added to a solvent mixture of 50 ml of toluene, 25 ml of ethanol and 25 ml of water and refluxed under heating and stirring for 2 hours. The resulting reaction mixture was poured into ice-cold water and extracted with toluene. The toluene layer was washed with water twice and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 1.3 g of [3-(4-trifluoromethylphenyl)phenyl] cyclopentyl sulfide (yield 78.0%) as a colorless liquid (nD20 1.5732).

Aufarbeitung

  1. temperaturerefluxed
  2. temperatureunder heating
  3. customThe resulting reaction mixture
  4. additionwas poured into ice-cold water
  5. extractionextracted with toluene
  6. washThe toluene layer was washed with water twice
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customPurification of the residue by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-04e4602c366d45ddbdb1050a3e7d0fb4
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858639B2

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