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

HRID 277000

Reaktionsgleichung

Reaktionsgleichung von HRID 277000
[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-ed1ba6631a054e9c8ebf9aa588c7baa7
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355648B1

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