4-Methoxyphenol → 3-(4-Methoxyphenoxy)benzo[b]thiophene

HRID 1386984

Reaktionsgleichung

Reaktionsgleichung von HRID 1386984
Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.[Cu]I>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:2]2[C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[S:5][CH:6]=2)=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 90154-MethoxyphenolHCID 11430Potassium CarbonateHCID 123250Benzo(b)thiophene, 3-bromo-

Produkt 1

HCID 108249753-(4-Methoxyphenoxy)benzo[b]thiophene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 4.00 g (19.7 mmol) of 3-bromobenzo[b]thiophene, 4.96 g (40 mmol) of 4-methoxyphenol, 5.52 g (40 mmol) of K2CO3, and 0.20 g (1.0 mmol) of CuI was heated to 140° C. and sonicated at this temperature for 2 h. The reaction was allowed to cool, taken up in CH2Cl2, and the mixture was washed several times with 0.5 N NaOH. The organic layer was dried over Na2SO4 and concentrated in vacuo to an oil that was subjected to chromatography (SiO2; gradient of 0-5% EtOAc in hexanes). The fractions containing the desired product were combined, evaporated in vacuo, and the residue was recrystallized from hexanes to afford 500 mg (1.95 mmol; 10%) of the title compound as a white solid.

Aufarbeitung

  1. customsonicated at this temperature for 2 h
  2. temperatureto cool
  3. washthe mixture was washed several times with 0.5 N NaOH
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated in vacuo to an oil that
  6. additionThe fractions containing the desired product
  7. customevaporated in vacuo
  8. customthe residue was recrystallized from hexanes

Quellen und Nachweise

ORD-Eintrag
ord-88fa74840acb457dbd2585d04240b8d3
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06265575B1

Verknüpfte Notizen

Wird geladen…