2-Bromobenzaldehyde → 2-((4-Methoxyphenyl)ethynyl)benzaldehyde

HRID 418855Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 418855
Br[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[CH:19])=[CH:14][CH:13]=1>C(N(CC)CC)C.[Cu]I>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[C:19][C:2]2[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])=[CH:14][CH:13]=1

Komponenten

5

Edukt 2

HCID 811292-BromobenzaldehydeHCID 2510201-Ethynyl-4-methoxybenzene

Produkt 1

HCID 129972402-((4-Methoxyphenyl)ethynyl)benzaldehydeAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8471TriethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-bromobenzaldehyde (1.85 g, 10 mmol) and 4-methoxyphenyl acetylene (1.58 g, 12 mmol) in 40 mL of triethylamine were added dichlorobis(triphenylphosphine) palladium(II) (140 mg, 2 mol %) and copper(I) iodide (20 mg, 1 mol %). The reaction mixture was heated at 50° C. under nitrogen for 3 h. The reaction mixture was cooled to room temperature and the ammonium salt was removed by filtration. The filtrate was concentrated under reduced pressure. Purification of the crude compound by column chromatography (SilicaGel 230-400 mesh; 10% ethyl acetate in hexanes as eluent) afforded of 2-(4-methoxy phenylethynyl)benzaldehyde (2.1 g, 89%).

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe ammonium salt was removed by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customPurification of the crude compound by column chromatography (SilicaGel 230-400 mesh; 10% ethyl acetate in hexanes as eluent)

Quellen und Nachweise

ORD-Eintrag
ord-42f87fc1d9d34de1a850a74154217349
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093273B2

Notizen zur Reaktion

Wird geladen…