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

HRID 6987Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 6987
[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 the subtitled compound, 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-099a937005364924bd6eae4d9b0b8422
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084168B2

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