8-Methylquinoline → 8-(Bromomethyl)quinoline

HRID 911344

Reaktionsgleichung

Reaktionsgleichung von HRID 911344
[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.C1C(=O)N([Br:19])C(=O)C1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:19][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 83,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Combine 8-methyl-quinoline (1.0 g, 6.99 mmol), NBS (1.3 g, 7.13 mmol), benzoyl peroxide (6.0 mg, 0.03 mmol), carbon tetrachloride (30 mL) and reflux for 17 h. Cool the reaction mixture to ambient temperature and evaporate the solvent. Dissolve the residue in chloroform (30 mL), wash the organic solution with saturated aqueous NaHCO3 (2×10 mL), brine (10 mL) and dry over anhydrous Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with DCM to obtain the title compound as a white solid (1.3 g, 83%). MS (ES+) m/z: 223 (M+H)+.

Aufarbeitung

  1. customevaporate the solvent
  2. dissolutionDissolve the residue in chloroform (30 mL)
  3. washwash the organic solution with saturated aqueous NaHCO3 (2×10 mL), brine (10 mL)
  4. dry with materialdry over anhydrous Na2SO4
  5. customEvaporate the solvent
  6. custompurify by chromatography on silica gel eluting with DCM

Quellen und Nachweise

ORD-Eintrag
ord-5f78717363864841a89c26a5b8c91846
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022062B2

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