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Carbon tetrabromide → 1-(2,2-Dibromovinyl)-3,5-diethoxybenzene

HRID 516144
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 516144
[C:1]([Br:5])(Br)(Br)[Br:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:25]([O:27][C:28]1[CH:29]=[C:30]([CH:33]=[C:34]([O:36][CH2:37][CH3:38])[CH:35]=1)[CH:31]=O)[CH3:26]>ClC(Cl)C.ClCCl>[Br:2][C:1]([Br:5])=[CH:31][C:30]1[CH:33]=[C:34]([O:36][CH2:37][CH3:38])[CH:35]=[C:28]([O:27][CH2:25][CH3:26])[CH:29]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 226086163,5-Diethoxybenzaldehyde

Produkt 1

HCID 898708271-(2,2-Dibromovinyl)-3,5-diethoxybenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6365
1,1-Dichloroethane
Lösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Carbon tetrabromide (4.78 g) was dissolved in dichloroethane (14 mL), and triphenylphosphine (7.56 g) was added thereto at 0° C. After stirring at 0° C. for 5 minutes, a solution of 3,5-diethoxybenzaldehyde (1.40 g) in dichloromethane (7 mL) was added thereto, followed by stirring for 20 minutes. Without performing further treatment, the reaction mixture was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate) to obtain 1-(2,2-dibromovinyl)-3,5-diethoxybenzene. The obtained compound was used for the subsequent reaction without further purification. The compound obtained above was dissolved in THF (30 mL). A 1.63 M n-butyllithium solution in hexane (10.5 mL) was added thereto at −78° C. The resulting mixture was stirred at −78° C. for 30 minutes. After adding a saturated aqueous ammonium chloride solution, the reaction mixture was subjected to extraction using ethyl acetate. The resulting organic layer was washed with a saturated sodium chloride solution, and the organic layer was then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: hexane/ethyl acetate) to obtain the title compound as a colorless, oily substance (1.31 g). Physical properties: m/z [M+H]+ 191.0

Aufarbeitung

  1. customat 0° C
  2. stirringby stirring for 20 minutes
  3. customthe reaction mixture was purified by silica gel chromatography (developing solvent: hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2fbc6c50f9b448a69f5a769bd0063331
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09108973B2

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