Rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one → 3-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

HRID 556447

Reaktionsgleichung

Reaktionsgleichung von HRID 556447
C1C=C[NH+]=CC=1.[Br:7][Br-]Br.[Cl:10][C:11]1[CH:19]=[C:18]2[C:14]([CH:15]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=3)[C:16](=[O:20])[NH:17]2)=[CH:13][CH:12]=1>CC(O)(C)C.O>[Br:7][C:15]1([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[C:14]2[C:18](=[CH:19][C:11]([Cl:10])=[CH:12][CH:13]=2)[NH:17][C:16]1=[O:20]

Komponenten

4

Edukt 1

HCID 57507272Rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one

Produkt 1

HCID 575072733-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-oneAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Pyridinium bromide perbromide (21.7 g, 68 mmol) (Aldrich) was added in one portion to a solution of rac-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (18 g, 62 mmol) (from example 1b supra) in t-BuOH (400 mL) and water (2 mL) at room temperature with stirring. After stirring at room temperature for 4 h, the mixture was diluted with water (500 mL) and stirred for 1 h. The resulting precipitate was collected and dried to give 22 g of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one as a pale yellow solid. MS: 371 (M+H)+.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 4 h
  2. stirringstirred for 1 h
  3. customThe resulting precipitate was collected
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-aa49005c630d4423905b6d0026cbce4b
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08058269B2

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