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Water → 2-Bromo-5-decylthiophene

HRID 545981
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 545981
[CH2:1]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[Br:16]N1C(=O)CCC1=O.O>CN(C=O)C>[Br:16][C:13]1[S:12][C:11]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10])=[CH:15][CH:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 67184N-bromobutanimide2×HCID 5663312-Decylthiophene

Produkt 1

HCID 588928162-Bromo-5-decylthiopheneAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Decylthiophene (52.8 g, 0.235 mol) prepared above and DMF (200 ml) were placed in a 1000-ml three-necked flask equipped with a 200-ml dropping funnel and a reflux tube. A solution of N-bromosuccinimide (hereinafter referred to as “NBS”) (44.0 g, 0.247 mol) in DMF (100 ml) was added dropwise to the solution at room temperature in an argon gas stream over a period of about one hr. After the completion of the dropwise addition, the mixture was stirred with heating at 100° C. for about 2 hr. After the completion of the reaction, water (300 ml) was added to the reaction solution, and the organic layer was extracted with diethyl ether, was dried over sodium sulfate, and was applied to column chromatography (n-hexane) to give an objective compound 2-bromo-5-decylthiophene as a yellow liquid (67.0 g, yield 94.0%). 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), 1.26 (m, 14H), 1.61 (m, 2H), 2.73 (t, 2H, J=7.32 Hz), 6.52 (d, 1H, J=3.90 Hz). 6.83 (d, 1H, J=3.90 Hz).

Aufarbeitung

  1. customwere placed in a 1000-ml three-necked flask
  2. customequipped with a 200-ml
  3. additionwas added dropwise to the solution at room temperature in an argon gas stream over a period of about one hr
  4. additionAfter the completion of the dropwise addition
  5. additionwas added to the reaction solution
  6. extractionthe organic layer was extracted with diethyl ether
  7. dry with materialwas dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-211bd03701af4a5a8ebf3f6fbf1803ca
Quelldatensatz
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07935828B2

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