1,1-Dibromo-1-pentene → HCID 70653185, Verbindung

HRID 2275394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2275394
C[Sn]1(C)[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:4]2[S:10][CH:11]=[CH:12][C:3]1=2.Br[C:15](Br)=[CH:16][CH2:17][CH2:18][CH3:19]>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:16](=[C:15]1[C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:4]2[S:10][CH:11]=[CH:12][C:3]1=2)[CH2:17][CH2:18][CH3:19]

Komponenten

5

Edukt 2

HCID 5340761,1-Dibromo-1-penteneHCID 86688839HCID 86688839, Verbindung

Produkt 1

HCID 70653185HCID 70653185, VerbindungAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418851HCID 178418851, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

500 mg (1.6 mmol) of 52 and 364 mg (1.6 mmol) of dibromopentene were dissolved in 32 ml of freshly distilled THF, and 42 mg (80 μmol) of bis(tri-tert-butylphosphine)palladium(0) were added. The reaction mixture was refluxed while stirring for 8 hours. THF was removed by rotary evaporation and the residue was taken up in n-hexane. The crude product was purified by means of column chromatography (n-hexane as the eluent (Rf=0.4)) to obtain 115 mg of the target compound 53 (37% yield). GC-MS m/z 232 (18.10 min).

Aufarbeitung

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed
  3. customTHF was removed by rotary evaporation
  4. customThe crude product was purified by means of column chromatography (n-hexane as the eluent (Rf=0.4))

Quellen und Nachweise

ORD-Eintrag
ord-d289abcd4d284d4ba8ed7126bc7a6281
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09127020B2

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