Potassium Hydroxide → 6-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline

HRID 1505743

Reaktionsgleichung

Reaktionsgleichung von HRID 1505743
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Br:9])=[CH:4][C:3]=1[CH2:10]O.[CH3:12][C:13]1[CH:18]=[C:17]([C:19]([CH3:21])=O)[CH:16]=[C:15]([CH3:22])[CH:14]=1.[OH-].[K+]>C1(C)C=CC=CC=1>[Br:9][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][C:6]=1[Cl:8])[N:1]=[C:19]([C:17]1[CH:18]=[C:13]([CH3:12])[CH:14]=[C:15]([CH3:22])[CH:16]=1)[CH:21]=[CH:10]2

Komponenten

5

Edukt 3

HCID 14797Potassium HydroxideHCID 149211-(3,5-Dimethylphenyl)ethan-1-oneHCID 67081018(2-Amino-5-bromo-4-chlorophenyl)methanol

Produkt 1

HCID 866849816-Bromo-7-chloro-2-(3,5-dimethylphenyl)quinolineAusbeute 43,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

(2-amino-5-bromo-4-chlorophenyl)methanol (8.2 g, 34.7 mmol), 3,5-dimethylacetophenone (8.22 g, 55.5 mmol), RuCl2(PPh3)3 (0.15 g, 0.173 mmol), and KOH (1.31 g, 23.4 mmol) was refluxed in 90 mL of toluene for 18 hours. Water was collected from the reaction using a Dean-Stark trap. The reaction mixture was allowed to cool to room temperature and filtered through a silica gel plug and eluted with DCM and purified by column chromatography, eluting with 2:1 (v/v) hexanes:DCM, to give 6-bromo-7-chloro-2-(3,5-dimethylphenyl)quinoline (5.2 g, 43.3%).

Aufarbeitung

  1. customWater was collected from the reaction
  2. filtrationfiltered through a silica gel plug
  3. washeluted with DCM
  4. custompurified by column chromatography
  5. washeluting with 2:1 (v/v) hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5b3c372cda554e3b92366ec5f333ff36
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09217004B2

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