Bromine → 5-Bromo-3,3-diethyl-1,3-dihydro-2H-indol-2-one

HRID 9328

Reaktionsgleichung

Reaktionsgleichung von HRID 9328
[CH2:1]([C:3]1([CH2:13][CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])[CH3:2].C([O-])(=O)C.[Na+].[Br:20]Br>C(O)(=O)C.O>[Br:20][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4](=[O:12])[C:3]2([CH2:1][CH3:2])[CH2:13][CH3:14]

Komponenten

6

Edukt 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 151532213,3-diethyl-2,3-dihydro-1H-indol-2-one

Produkt 1

HCID 219862505-Bromo-3,3-diethyl-1,3-dihydro-2H-indol-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 3,3-diethylindol-2-one (8 g, 40 mmol) and sodium acetate (4 g, 48 mmol) in acetic acid (100 ml) was treated with bromine (6.4 g, 40 mmol). After 30 min. the mixture was diluted with water and extracted with EtOAc (2×); the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, then brine, dried (MgSO4) and evaporated to afford the crude product (7.6 g, 75%). A sample was recrystallized from EtOAc/hexane to obtain 5-bromo-1,3-dihydro-3,3-diethyl-[2H]-indol-2-one, m.p. 164–165° C.; 1H-NMR (DMSO-d6) δ 10.45 (s, 1H), 7.41–7.40 (d, 1H, J=2.2 Hz), 7.34–7.31 (m, 1H), 6.78–6.76 (d, 1H, J=8.2 Hz), 1.78–1.65 (m, 4H), 0.50–0.46 (m, 6H); MS (−ESI) m/z 266/268 (M−H).

Aufarbeitung

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution
  3. dry with materialbrine, dried (MgSO4)
  4. customevaporated
  5. customto afford the crude product (7.6 g, 75%)
  6. customA sample was recrystallized from EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-556c1aea34984edebf71a28e879e10a3
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091234B2

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