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

HRID 78501Notes

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

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

customquenched with NaHCO3 powder in small portions
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-94087592dc1d481b883e9e100d015ab9
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841334B2

Reaction notes

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