Water → 3-Bromo-1-(P-toluenesulfonyl)indole

HRID 478197Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 478197
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[S:11](Cl)([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12].[OH-].[Na+].O>C1C=CC=CC=1.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 27632773-Bromo-1h-indole

Produkt 1

HCID 112102743-Bromo-1-(P-toluenesulfonyl)indoleAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 241BenzeneLösungsmittel

Versuchsvorschrift

To a solution of 3-bromoindole (prepared according to the method described in Synthesis, 1096(1982)) (196 mg, 1.0 mmol) and tosyl chloride (286 mg, 1.5 mmol) in benzene (4.5 mL) was added tetra-n-butylammonium hydrogensulfate (34 mg, 0.1 mmol) and a 5.0% aqueous sodium hydroxide (1.0 mL), and the resulting mixture was refluxed for 1 hour. After the reaction solution was cooled to room temperature, water was added to the reaction solution, and the resulting mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the chloroform layer was concentrated, and the resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1) to afford the title compound (335 mg, yield: 96%) as white crystals.

Aufarbeitung

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. concentrationthe chloroform layer was concentrated
  4. customthe resulting crude product was purified by column chromatography on a silica gel (eluent; hexane:ethyl acetate=6:1)

Quellen und Nachweise

ORD-Eintrag
ord-d4eccb9a4fc145d0b357794e9d169fb4
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642228B1

Notizen zur Reaktion

Wird geladen…