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Hydrochloric Acid → 5-Decyl-2,2'-bithiophene

HRID 545982
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 545982
[Mg].Br[C:3]1[S:4][CH:5]=[CH:6][CH:7]=1.Br[C:9]1[S:10][C:11]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][CH:13]=1.Cl>C1COCC1>[CH2:14]([C:11]1[S:10][C:9]([C:3]2[S:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:12]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 138512-BromothiopheneHCID 5462224MagnesiumHCID 588928162-Bromo-5-decylthiophene

Produkt 1

HCID 588928175-Decyl-2,2'-bithiopheneAusbeute 65.934,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Versuchsvorschrift

Magnesium (8.90 g, 0.365 mmol) and THF (100 ml) were placed in a 300-ml flask equipped with a reflux tube. A solution of 2-bromothiophene (54.0 g, 0.332 mmol) in THF (100 ml) was slowly added drowpwise thereto, and the mixture was heated under reflux for about 2 hr to prepare a Grignard reagent. This Grignard reagent was added dropwise to a mixed solution composed of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex (1:1) (1.80 g, 2.21 mmol), 2-bromo-5-decylthiophene (67.0 g, 221 mmol) prepared above, and THF (100 ml) at about 0° C. After the completion of the dropwise addition, the mixture was stirred at room temperature overnight. After the completion of the reaction, 1 N HCl (200 ml) was added to the reaction solution, and the organic layer was extracted with chloroform, was dried over sodium sulfate, and was applied to column chromatography (n-hexane) to give an objective compound 5-decyl-2,2′-bithiophene as a light yellow solid (67.1 g, yield 99.1%). An NMR spectrum of the compound thus obtained was measured at room temperature with an NMR spectrometer (model JNM-LA400W, manufactured by Japan Electric Optical Laboratory). 1H-NMR (CDCl3, TMS/ppm): 0.88 (t, 3H, J=6.83 Hz), 1.31 (m, 14H), 1.67 (m, 2H), 2.78 (t, 2H, J=7.32 Hz), 6.67 (d, 1H, J=3.90 Hz), 6.98 (m, 2H), 7.09 (d, 1H, J=3.90 Hz), 7.15 (d, 1H, J=4.88 Hz)

Aufarbeitung

  1. customequipped with a reflux tube
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for about 2 hr
  4. additionAfter the completion of the dropwise addition
  5. additionwas added to the reaction solution
  6. extractionthe organic layer was extracted with chloroform
  7. dry with materialwas dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-98f6ed1420244e34aea5f8df36c7dda3
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935828B2

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