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Bromine → 2-(5-Bromo-6-hydroxy-2-naphthyl)-3-pentyl-1H-indole

HRID 495499
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 495499
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[NH:13][C:14]3[C:19]([C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=[CH:5]2.CC([O-])=O.[K+].[Br:31]Br>CC(O)=O.O>[Br:31][C:3]1[C:2]([OH:1])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([C:12]1[NH:13][C:14]3[C:19]([C:20]=1[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:8]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 24408BromineHCID 517044Potassium AcetateHCID 223273352-(6-Hydroxy-2-naphthyl)-3-pentyl-1H-indole

Produkt 1

HCID 223273382-(5-Bromo-6-hydroxy-2-naphthyl)-3-pentyl-1H-indoleAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittel2×
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(6-hydroxy-2-naphthyl)-3-pentyl-1H-indole (1.27 g, 3.85 mmol) in HOAc (25 mL) at 0° C. was added KOAc (0.453 g, 4.62 mmol). The reaction was stirred at this temperature for 10 min., and then a solution of Br2 (0.218 mL, 4.24 mmol) in HOAc (5 mL) was added dropwise to it over a period of ˜10 min. The reaction mixture was allowed to warm to rt and stirred for 4 h. The reaction mixture was then diluted with H2O (50 mL) and extracted with EtOAc (200 mL). The organic layer was washed with brine (20 mL) and then dried (Na2SO4). After concentration, the residue was purified by the Biotage Flash 40 apparatus (10 to 30% EtOAc:petroleum ether gradient) to afford the product (0.782 g, 50%) as a solid (inseparable mixture of mono- and di-bromo-substituted analogs which were separated in the next step); monobrominated compound: mass spectrum [(−) ESI], m/z 406/408 (M−H)− and dibrominated analog: mass spectrum [(−) ESI], m/z 486 (M−H)−.

Aufarbeitung

  1. stirringstirred for 4 h
  2. extractionextracted with EtOAc (200 mL)
  3. washThe organic layer was washed with brine (20 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentration
  6. customthe residue was purified by the Biotage Flash 40 apparatus (10 to 30% EtOAc:petroleum ether gradient)

Quellen und Nachweise

ORD-Eintrag
ord-0df7902b4cff47f89dcde1348a435210
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06939886B2

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