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

HRID 1037923Notes

Reaction equation

HRID 1037923 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-2b7c1749d42d412e8e3ac3e54b2dd5eb
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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