1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-6-fluoroindole

HRID 51014

Reaktionsgleichung

Reaktionsgleichung von HRID 51014
Br[CH2:2][CH2:3][CH2:4][Cl:5].[F:6][C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][NH:13]2)=[CH:9][CH:8]=1.[OH-].[K+]>CN(C=O)C>[Cl:5][CH2:4][CH2:3][CH2:2][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([F:6])[CH:15]=2)[CH:11]=[CH:12]1

Komponenten

5

Edukt 3

HCID 80061-Bromo-3-chloropropaneHCID 14797Potassium HydroxideHCID 3512786-Fluoroindole

Produkt 1

HCID 227358421-(3-Chloropropyl)-6-fluoroindoleAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a solution of 1-bromo-3-chloropropane (700 mg, 4.44 mmol) in DMF (2.4 mL) was added 6-fluoroindole (200 mg, 1.48 mmol) and powder KOH (92 mg, 1.63 mmol) at 20° C. The reaction mixture was stirred for 15 h at 20° C. then quenched by addition of H2O and extracted with Et2O. The combined organic solution was successively washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was chromatographed to give 1-(3-chloropropyl)-6-fluoroindole (190 mg, 66%) as a colorless oil.

Aufarbeitung

  1. customthen quenched by addition of H2O
  2. extractionextracted with Et2O
  3. washThe combined organic solution was successively washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-f8f8abdedbe44766b4744b3242669eaa
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713471B1

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