Bromine → Methyl 4-bromo-5-ethyl-2-furancarboxylate

HRID 1961174Notes

Reaction equation

HRID 1961174 reaction equation
[CH2:1]([C:3]1[O:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][CH:4]=1)[CH3:2].[Cl-].[Cl-].[Cl-].[Al+3].[Br:16]Br>C(Cl)(Cl)Cl>[Br:16][C:4]1[CH:5]=[C:6]([C:8]([O:10][CH3:11])=[O:9])[O:7][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 6451240Aluminum(III) ChlorideHCID 13637632Methyl 5-ethylfuran-2-carboxylate

Product 1

HCID 57826652Methyl 4-bromo-5-ethyl-2-furancarboxylateYield 41.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 5-ethyl-2-furancarboxylate (1.2 g, 7.78 mmol) and aluminum trichloride (1.56 g, 11.68 mmol) in chloroform (15 ml) at 25° C. was added bromine (0.56 ml, 10.90 mmol). The resulting solution stirred at 70° C. in a sealed tube for 2 h and the solution was cooled, concentrated and purified via column chromatography (silica, 5% EtOAc in hexanes) affording methyl 4-bromo-5-ethyl-2-furancarboxylate (1.1 g, 3.26 mmol, 41.8% yield) as a white solid; LCMS (ES) m/z=233, 235 (M, M+2)+.

Workup

  1. temperaturethe solution was cooled
  2. concentrationconcentrated
  3. custompurified via column chromatography (silica, 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d1a6500b93644914afcceb0cc6da012a
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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