Water → 2-Acetylindole

HRID 631786Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631786
Cl[Sn](Cl)(Cl)Cl.Br[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2.[C:16](Cl)(=[O:18])[CH3:17].O>C1(C)C=CC=CC=1>[C:16]([C:11]1[NH:12][C:13]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:15][CH:14]=2)(=[O:18])[CH3:17]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24287Tin tetrachlorideHCID 249055-Bromoindole

Produkt 1

HCID 5890812-AcetylindoleAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 1.0 M solution of SnCl4 (10 mL, 10.0 mmol) was added to a stirred solution of 5-bromoindole (ab) (980 mg, 5.0 mmol) and acetyl chloride (0.714 mL, 785 mg, 10.0 mmol) in 20 mL of dry toluene at 0° C. The resulting mixture was stirred at room temperature during 4 hours, and then 50 ml, of water was added. The mixture was extracted with EtOAc (3×20 mL) and the collected organic layers were washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated under vacuum. Column chromatography using EtOAc-pentane (from 5/95 to 80/20) yielded pure acetylindole (jb) (1.0 g, 4.2 mmol) as a white solid. Yield: 84%.

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (3×20 mL)
  2. washthe collected organic layers were washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6642dd0c19c644dbb3b22c56ace4d73f
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321722B2

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