1,2-Bis(chloromethyl)benzene → 7-Chloro-2-[5-(2-chloromethylbenzyloxy)benzofuran-2-yl]quinoline

HRID 2258508Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2258508
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[H-].[Na+].[Cl:24][CH2:25][C:26]1[C:27]([CH2:32]Cl)=[CH:28][CH:29]=[CH:30][CH:31]=1>O1CCCC1>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12]3[O:13][C:14]4[CH:20]=[CH:19][C:18]([O:21][CH2:32][C:27]5[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=5[CH2:25][Cl:24])=[CH:17][C:15]=4[CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 119191,2-Bis(chloromethyl)benzeneHCID 24758Sodium hydrideHCID 229222067-Chloro-2-(5-hydroxybenzofuran-2-yl)quinoline

Produkt 1

HCID 229221307-Chloro-2-[5-(2-chloromethylbenzyloxy)benzofuran-2-yl]quinolineAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a cooled suspension of 7-chloro-2-(5-hydroxybenzofuran-2-yl)quinoline (0.71 g) in tetrahydrofuran (12 ml), sodium hydride (60% in mineral oil, 0.125 g) was added below 10° c. After being stirred for 15 minutes, α,α'-dichloro-o-xylene (1.68 g) was added to the mixture. After subsequently being stirred at ambient temperature for 1.5 hours, the mixture was refluxed for 25 hours. After the solvent was removed under reduced pressure, the residue was subjected to column chromatography on silica gel (25 g) and eluted with a mixture of chloroform and n-hexane (1:1). The fractions containing object compound were combined and concentrated under reduced pressure give 7-chloro-2-[5-(2-chloromethylbenzyloxy)benzofuran-2-yl]quinoline (0.56 g).

Aufarbeitung

  1. additionwas added below 10° c
  2. stirringAfter subsequently being stirred at ambient temperature for 1.5 hours
  3. temperaturethe mixture was refluxed for 25 hours
  4. customAfter the solvent was removed under reduced pressure
  5. washeluted with a mixture of chloroform and n-hexane (1:1)
  6. additionThe fractions containing object compound
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c1a55532f34b45df9775bc1eb7f8cf9c
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05661159

Notizen zur Reaktion

Wird geladen…