Water → 5-Bromo-2-oxindole

HRID 6979

Reaktionsgleichung

Reaktionsgleichung von HRID 6979
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C([O-])(=O)C.[Na+].[Br:16]Br.O>C(Cl)(Cl)Cl.CCOC(C)=O>[Br:16][C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][C:2](=[O:10])[CH2:3]2

Komponenten

7

Edukt 4

HCID 962WaterHCID 24408BromineHCID 321710OxindoleHCID 517045Sodium Acetate

Produkt 1

HCID 6111935-Bromo-2-oxindoleAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of oxindole (2.0 g, 15.0 mmol) and sodium acetate (2.1 g, 25.5 mmol) in CHCl3 (20 cm3) was treated with bromine (2.4 g, 15.0 mmol) in CHCl3 (10 cm3). After 30 min. the mixture was allowed to warm to RT and stirred for 1 h. The reaction mixture was diluted with EtOAc (500 cm3) and poured into water. The aqueous layer was extracted with EtOAc (×2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine, dried (MgSO4), and evaporated to give the title compound (3.1 g, 14.6 mmol, 96%) as an off-white solid which was used without further purification: m.p. 221–223° C.; 1H NMR (DMSO-d6) δ 3.51 (s, 2H), 6.76 (d, 1H, J=8.1 Hz), 7.33(dd, 1H, J=8.1, 1.7 Hz), 7.37 (s, 1H), 10.49 (br s, 1H); 13C NMR (DMSO-d6) δ 36.10 (t), 111.21 (d), 113.16 (s), 127.54 (d), 128.3 (s), 130.40 (d), 143.34 (s), 176.24 (s); MS (EI) m/z 211, 213 (M)+.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with EtOAc (×2)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-fbb70cf1aa6d4f91b0623384d82a6ec4
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084168B2

Verknüpfte Notizen

Wird geladen…