8-Methylquinoline → 8-(Bromomethyl)quinoline

HRID 327435

Reaktionsgleichung

Reaktionsgleichung von HRID 327435
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:12][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Komponenten

5

Edukt 2

HCID 119108-MethylquinolineHCID 67184N-bromobutanimide

Produkt 1

HCID 3469148-(Bromomethyl)quinolineAusbeute 54,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 8-methylquinoline (45 g, 0.314 mol), N-bromosuccinimide (55 g, 0.309 mol) and benzoyl peroxide (1.5 g) in carbon tetrachloride (250 mL) was refluxed for 7 hours. The reaction was filtered and evaporated, and the crude product was crystallized from methanol (70 mL) to give 37.7 g of product. The mother liquors were chromatographed on silica gel in chloroform to give 17 g of material which was crystallized from ethyl acetate:hexane to give an additional 12.0 g of product.

Aufarbeitung

  1. temperaturewas refluxed for 7 hours
  2. filtrationThe reaction was filtered
  3. customevaporated
  4. customthe crude product was crystallized from methanol (70 mL)

Quellen und Nachweise

ORD-Eintrag
ord-b7ace455fc304e83b893bd03f7303095
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05273975

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