Indole → 1-(2-chloroethyl)-1H-indole

HRID 1798015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1798015
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Br[CH2:13][CH2:14][Cl:15].O>CCCCC.CN(C=O)C>[Cl:15][CH2:14][CH2:13][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Komponenten

7

Edukt 4

HCID 798IndoleHCID 962WaterHCID 78491-Bromo-2-ChloroethaneHCID 24758Sodium hydride2×

Produkt 1

HCID 108992601-(2-chloroethyl)-1H-indoleAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8003PentaneLösungsmittel

Versuchsvorschrift

NaH (0.253 g; 0.11 mole of 60% NaH in suspension in mineral oil, previously washed with pentane) is added to a solution of indole (1.17 g; 0.1 mole) in 10 mL of DMF placed under a nitrogen atmosphere, then the reaction mixture is stirred for 30 minutes at ambient temperature. 1-bromo 2-chloroethane is then added. After reaction for 2 hours, the reaction mixture is treated by the slow addition of water and extracted with ethyl acetate. The organic phase is washed with water then with a saturated aqueous solution of NaCl, dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The residue obtained is purified by chromatography on silica gel. The 1-(2-chloroethyl)indole is obtained pure with a yield of 80%.

Aufarbeitung

  1. customAfter reaction for 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with water
  4. dry with materialwith a saturated aqueous solution of NaCl, dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-a866812d3a264815a7c3a655b5b17cd0
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08343964B2

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