Citraconic Anhydrides → 3-BroMo-4-Methylfuran-2,5-dione

HRID 249990

Reaction equation

HRID 249990 reaction equation
[CH3:1][C:2]1[C:3](=[O:8])[O:4][C:5](=[O:7])[CH:6]=1.[Al](Br)(Br)[Br:10].BrBr>C(OCC)(=O)C>[Br:10][C:6]1[C:5](=[O:7])[O:4][C:3](=[O:8])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 12012Citraconic AnhydridesHCID 24408BromineHCID 24409Aluminum bromide

Product 1

HCID 105838543-BroMo-4-Methylfuran-2,5-dioneYield 9,023.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 3-methyl-2,5-furandione (citraconic anhydride, 1 g), AlBr3 (26 mg) and Br2 (0.46 mL) was heated at 120° C. overnight. Ethyl acetate was then added and the organic phase was washed with HCl 0.1% and then with brine. The organic phase was dried and concentrated in vacuo to give the crude product (1.680 g) that was used without further purification.

Workup

  1. washthe organic phase was washed with HCl 0.1%
  2. customThe organic phase was dried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7740d3fce82847729128eaba9969fa7f
Source dataset
uspto-grants-2011_01
Patent number
US07863299B2

Linked notes

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