4-Bromothiophene-3-carboxaldehyde → HCID 22503031, Verbindung

HRID 1814492

Reaktionsgleichung

Reaktionsgleichung von HRID 1814492
[CH:1]([C:3]1[C:7](Br)=[CH:6][S:5][CH:4]=1)=[O:2].[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1>CN(C=O)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.C(N(CC)CC)C>[CH3:9][O:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]#[C:20][C:7]2[C:3]([CH:1]=[O:2])=[CH:4][S:5][CH:6]=2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 2

HCID 27642074-Bromothiophene-3-carboxaldehydeHCID 225029951-Ethynyl-4-(methoxymethoxy)benzene

Produkt 1

HCID 22503031HCID 22503031, VerbindungAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-Formyl-4-bromothiophene (14.7 g) was dissolved in DMF (100 ml), followed by the addition of triethylamine (100 ml) CuI (0.25 g), Pd(PPh3)2Cl2 (0.5 g) and 4-methoxymethoxy-1-ethynylbenzene (11.4 g), and the mixture was reacted at 70° C. overnight. The reaction solution was filtered through Celite, poured into 1N hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine, dried and evaporated. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system), to give 3-{[4-(methoxymethoxy)phenyl]ethynyl}-4-formylthiophene as a colorless oil (12.8 g, yield; 47%).

Aufarbeitung

  1. customthe mixture was reacted at 70° C. overnight
  2. filtrationThe reaction solution was filtered through Celite
  3. additionpoured into 1N hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with an aqueous solution of saturated sodium bicarbonate and brine
  6. customdried
  7. customevaporated
  8. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate system)

Quellen und Nachweise

ORD-Eintrag
ord-0246105bfa19470789925f21a1f1695b
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06875761B2

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