Ethanedioyl dibromide → 4-Bromo-5,5-dimethylfuran-2-one

HRID 333364

Reaction equation

HRID 333364 reaction equation
O[C:2]1[C:6]([CH3:8])([CH3:7])[O:5][C:4](=[O:9])[CH:3]=1.C(Br)(=O)C([Br:13])=O>ClCCCl.CN(C=O)C>[Br:13][C:2]1[C:6]([CH3:8])([CH3:7])[O:5][C:4](=[O:9])[CH:3]=1

Participants

5

Reactant 2

HCID 84841Ethanedioyl dibromideHCID 547201394-Hydroxy-5,5-dimethyl-2(5H)-furanone

Product 1

HCID 126719604-Bromo-5,5-dimethylfuran-2-oneYield 86.2%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-hydroxy-5,5-dimethyl-5H-furan-2-one (2.1 g, 16.4 mmol) in DCE (40 mL) and DMF (1.5 mL) at 0° C. was added dropwise oxalyl bromide (3.0 mL, 32 mmol, 2 equiv). The mixture was stirred at room temperature for 4-5 h, and then put in an ice bath. Ice water (100 mL) was added slowly. The mixture was extracted with CH2Cl2 (100 mL). The organic phase was washed with 10% NaHCO3 and again with water, dried over sodium sulfate and evaporated to give the title compound 2.7 g (86% yield).

Workup

  1. customput in an ice bath
  2. extractionThe mixture was extracted with CH2Cl2 (100 mL)
  3. washThe organic phase was washed with 10% NaHCO3 and again with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-81dcf85130a4439ebe11d250cf52341f
Source dataset
uspto-grants-2014_11
Patent number
US08877923B2

Linked notes

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