Benzene, 1-bromo-3-iodo- → 4-(3-Bromophenyl)but-3-yn-1-ol

HRID 720835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 720835
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[CH2:9]([OH:13])[CH2:10][C:11]#[CH:12]>C(#N)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[C:4]([C:12]#[C:11][CH2:10][CH2:9][OH:13])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 11561Benzene, 1-bromo-3-iodo-HCID 135663-Butyn-1-OL

Produkt 1

HCID 218954424-(3-Bromophenyl)but-3-yn-1-ol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A stirred, cooled solution of 1-bromo-3-iodobenzene (31 g) and 3-butyn-ol (7 ml) in acetonitrile (100 ml) and triethylamine (100 ml) was purged with nitrogen for 20 min under nitrogen. Dichlorobis(triphenylphosphine)palladium (500 mg) and cuprous iodide (800 mg) were added. The mixture was stirred for 18 h and then the solvent was removed in-vacuo. The residual oil was triturated with ethyl acetate (200 ml) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on Biotage (90 g) eluting with light petroleum 40–60°-diethyl ether (3:2) to give the title compound (21 g). LCMS RT=3.26 min.

Aufarbeitung

  1. customwas purged with nitrogen for 20 min under nitrogen
  2. additionDichlorobis(triphenylphosphine)palladium (500 mg) and cuprous iodide (800 mg) were added
  3. customthe solvent was removed in-vacuo
  4. customThe residual oil was triturated with ethyl acetate (200 ml)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromatography on Biotage (90 g)
  8. washeluting with light petroleum 40–60°-diethyl ether (3:2)

Quellen und Nachweise

ORD-Eintrag
ord-f2c65a41e57b430cb116ded7b6632cf0
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07135600B2

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