Carbon tetrabromide → HCID 23019643, Verbindung

HRID 1354197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1354197
[CH:1]1([C:4]2[CH:5]=[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:7](=[O:23])[N:8]3[C:13]=2[C:12]([CH3:14])=[C:11]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21]O)=[CH:17][CH:16]=2)[CH:10]=[CH:9]3)[CH2:3][CH2:2]1.C(Br)(Br)(Br)[Br:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[Br:30][CH2:21][C:18]1[CH:19]=[CH:20][C:15]([C:11]2[CH:10]=[CH:9][N:8]3[C:13]([C:12]=2[CH3:14])=[C:4]([CH:1]2[CH2:3][CH2:2]2)[CH:5]=[C:6]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:7]3=[O:23])=[CH:16][CH:17]=1

Komponenten

5

Edukt 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 23019641HCID 23019641, Verbindung

Produkt 1

HCID 23019643HCID 23019643, VerbindungAusbeute 76,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

327 mg of ethyl 1-cyclopropyl-8-(4-hydroxymethylphenyl)-9-methyl-4-oxo-4H-quinolizine-3-carboxylate (Example 51) was dissolved in 11 ml of dichloromethane. 380 mg of carbon tetrabromide was added to the obtained solution, and they were cooled to 0° C. 355 mg of triphenylphosphine was added to the reaction mixture, and they were stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure. The obtained residue was purified by the silica gel column chromatography (eluent: hexane/ethyl acetate=1/1) to obtain 291 mg of ethyl 8-(4-bromomethylphenyl)-1-cyclopropyl-9-methyl-4-oxo-4H-quinolizine-3-carboxylate.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe obtained residue was purified by the silica gel column chromatography (eluent: hexane/ethyl acetate=1/1)

Quellen und Nachweise

ORD-Eintrag
ord-f5f38ffec10e4d36a84ecac0ed5fdc3e
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223773B2

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