Bromine → 4-Bromo-2,2,5,5-tetramethyldihydrofuran-3(2h)-one

HRID 78501

Reaktionsgleichung

Reaktionsgleichung von HRID 78501
[CH3:1][C:2]1([CH3:10])[C:6](=[O:7])[CH2:5][C:4]([CH3:9])([CH3:8])[O:3]1.[Br:11]Br>C(Cl)Cl>[Br:11][CH:5]1[C:4]([CH3:9])([CH3:8])[O:3][C:2]([CH3:10])([CH3:1])[C:6]1=[O:7]

Komponenten

4

Edukt 2

HCID 24408BromineHCID 1385112,2,5,5-Tetramethyltetrahydro-3-ketofuran

Produkt 1

HCID 122017454-Bromo-2,2,5,5-tetramethyldihydrofuran-3(2h)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of commercially available 2,2,5,5-tetramethyldihydrofuran-3(2H)-one (Aldrich, 10.0 g, 0.07 mol) in CH2Cl2 (100 mL) was added bromine (Aldrich, 3.6 mL, 0.07 mol,) dropwise at room temperature. The reaction mixture was stirred for 2 hours over which time the reaction mixture became clear. Then, the reaction mixture was cooled to 0° C., quenched with NaHCO3 powder in small portions, filtered and concentrated under reduced pressure to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 1.26 (s, 3H), 1.27 (s, 3H), 1.30 (s, 3H), 1.39 (s, 3H), 5.22 (s, 1H).

Aufarbeitung

  1. customquenched with NaHCO3 powder in small portions
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-94087592dc1d481b883e9e100d015ab9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841334B2

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