4-Iodoanisole → 1,2-Bis(4-methoxyphenyl)ethyne

HRID 351445Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351445
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[CH:10])=[CH:5][CH:4]=1.I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]#[C:10][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 696764-IodoanisoleHCID 2510201-Ethynyl-4-methoxybenzene

Produkt 1

HCID 6172341,2-Bis(4-methoxyphenyl)ethyne

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8021DiethylamineLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the solution of 4-methoxy-phenyl-acetylene (10 g, 0.075 mol) and 4-iodo-anisole (17.65 g, 1.0 eq.) in diethylamine (150 mL) was added Pd(PPh3)2Cl2 (2.65 g, 0.05 eq.) and the reaction mixture was stirred for 30 min at 0° C. To the reaction mixture was then added Cul (1.43 g, 0.1 eq.) and the mixture was stirred at 6 h at 0˜25° C. The reaction mixture was then concentrated and partitioned between ethyl acetate/H2O (200/600 mL). The organic layer was separated, dried and purified on SiO2 (1˜5% ethyl acetate/hexane) to yield 1,2-di(4-methoxy-phenyl)-acetylene.

Aufarbeitung

  1. stirringadded Cul (1.43 g, 0.1 eq.) and the mixture was stirred at 6 h at 0˜25° C
  2. concentrationThe reaction mixture was then concentrated
  3. custompartitioned between ethyl acetate/H2O (200/600 mL)
  4. customThe organic layer was separated
  5. customdried
  6. custompurified on SiO2 (1˜5% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-e9513de49e014efb8d3ccf28d7b9a302
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07183445B2

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