Ammonium Chloride → Diethyl 2,5-di(thiophen-2-yl)terephthalate

HRID 1755506Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755506
Br[C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10](Br)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br-].[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[Zn+].[NH4+].[Cl-]>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:2]1[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:10]([C:21]2[S:20][CH:24]=[CH:23][CH:22]=2)=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 22146229Diethyl 2,5-dibromobenzene-1,4-dicarboxylateHCID 178419761HCID 178419761, Verbindung

Produkt 1

HCID 59383235Diethyl 2,5-di(thiophen-2-yl)terephthalateAusbeute 80,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysator

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Diethyl 2,5-dibromoterephthalate (4.27 g, 11.24 mmol) and 2-thienylzinc bromide (0.5 M in THF, 50 ml, 25 mmol) are introduced into a two necked flask. The catalyst palladium tetrakis(triphenylphosphine) (Pd(PPh3)4) is then introduced into the two necked flask. The mixture thereby obtained is heated to reflux (70° C.) for 3 h. After a return to ambient temperature, the reaction mixture is poured into a saturated solution of NH4Cl. The product is extracted with ethyl acetate (3×100 ml). The extracts are combined and washed with water then dried on Na2SO4. After filtration, the solvent is removed under reduced pressure. The crude product is purified on chromatography column (silica gel, hexane/dichloromethane, 10:1, v/v)) to provide a white solid (3.5 g, 80%).

Aufarbeitung

  1. customThe mixture thereby obtained
  2. temperatureis heated
  3. extractionThe product is extracted with ethyl acetate (3×100 ml)
  4. washwashed with water
  5. customthen dried on Na2SO4
  6. filtrationAfter filtration
  7. customthe solvent is removed under reduced pressure
  8. customThe crude product is purified on chromatography column (silica gel, hexane/dichloromethane, 10:1

Quellen und Nachweise

ORD-Eintrag
ord-ce74fd1e2d98408388c1ebafacc408be
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09171676B2

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