Toluene → tert-butyl 4,5-dibromo-2-furancarboxylate

HRID 2109384Notes

Reaction equation

HRID 2109384 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[O:5][C:6]=1[Br:7].[C:11]1([CH3:17])[CH:16]=CC=C[CH:12]=1>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][C:11]([CH3:17])([CH3:16])[CH3:12])=[O:9])[O:5][C:6]=1[Br:7]

Participants

3

Reactant 2

HCID 1140Toluene2×HCID 41948324,5-Dibromofuran-2-carboxylic acid

Product 1

HCID 10616079tert-butyl 4,5-dibromo-2-furancarboxylate

Conditions

Temperature
90 °C

Procedure

A mixture composed of 4,5-dibromo-2-furancarboxylic acid (20.00 g), DMF di-tert-butylacetal (71.08 ml) and toluene (100 ml) was stirred for 2 hours at 90° C. The reaction solution was diluted with toluene and washed with 10% aqueous citric acid solution and saturated brine. The organic layer was dried over MgSO4, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20), thereby giving 20.10 g of tert-butyl 4,5-dibromo-2-furancarboxylate.

Workup

  1. washwashed with 10% aqueous citric acid solution and saturated brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/20)

Sources & evidence

ORD record
ord-63310cca935843c69cc6b09f72285152
Source dataset
uspto-grants-2009_04
Patent number
US07514452B2

Reaction notes

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