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Thionyl Chloride → 1-(Chloromethyl)-4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzene

HRID 875344
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 875344
S(Cl)([Cl:3])=O.[F:5][C:6]([F:24])([F:23])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=2)=[CH:9][CH:8]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:3][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][CH2:13][C:10]2[CH:11]=[CH:12][C:7]([C:6]([F:24])([F:23])[F:5])=[CH:8][CH:9]=2)=[CH:16][CH:17]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 86709834(4-{2-[4-(Trifluoromethyl)phenyl]ethyl}phenyl)methanol

Produkt 1

HCID 207707551-(Chloromethyl)-4-{2-[4-(trifluoromethyl)phenyl]ethyl}benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

At 0° C., 3.78 ml of thionyl chloride in 30 ml of dichloromethane were slowly added dropwise to a solution of 9.69 g (34.57 mmol) of (4-{2-[4-(trifluoromethyl)phenyl]ethyl}phenyl)methanol in 100 ml of dichloromethane. After the addition had ended, the reaction mixture was warmed to room temperature and stirred at this temperature for two hours. The reaction mixture was then once more cooled to 0° C., and 100 ml of saturated aqueous sodium bicarbonate solution were added slowly and carefully with vigorous stirring until a pH of 6 had been reached. The phases were then separated, and the organic phase was dried over magnesium sulphate, filtered and concentrated to dryness. This gave 8.64 g (28.92 mmol, 84% of theory) of the title compound.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureThe reaction mixture was then once more cooled to 0° C.
  3. stirringcarefully with vigorous stirring until a pH of 6
  4. customThe phases were then separated
  5. dry with materialthe organic phase was dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a1796249a81d47b29cd9c091f9c206eb
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08981104B2

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