1-Bromo-2-nitrobenzene → 4-(2-Nitrophenyl)but-3-yn-1-ol

HRID 342188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342188
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH2:11]([OH:15])[CH2:12][C:13]#[CH:14]>C(N(CC)CC)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Cu]I>[N+:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:14]#[C:13][CH2:12][CH2:11][OH:15])([O-:10])=[O:9]

Komponenten

6

Edukt 2

HCID 113411-Bromo-2-nitrobenzeneHCID 135663-Butyn-1-OL

Produkt 1

HCID 117454514-(2-Nitrophenyl)but-3-yn-1-olAusbeute 78,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of o-bromonitrobenzene (8.1 g, 0.04 mol) in 160 ml of triethylamine, under nitrogen, is treated sequentially with bis(triphenylphosphine)palladium(II)chloride (0.28 g, 0.4 mmol), 3-butyne-1-ol (2.81 g, 0.04 mol) and copper(I)iodide (0.15 g, 0.8 mmol), stirred for about 16 hours and filtered. The filtercake is washed with toluene. The filtrates are combined and concentrated in vacuo to give the title product as a dark oil, 6.0 g, 78.5% yield, identified by NMR and mass spectral analyses.

Aufarbeitung

  1. filtrationfiltered
  2. washThe filtercake is washed with toluene
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-828cf1896fe146b193c3ca0f64405f32
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856576

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