Water → Methyl 4-bromo-5-methylfuran-2-carboxylate

HRID 2392203Notes

Reaction equation

HRID 2392203 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Br:15]Br.O>C(Cl)(Cl)Cl>[Br:15][C:3]1[CH:4]=[C:5]([C:7]([O:9][CH3:10])=[O:8])[O:6][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 137628Methyl 5-methyl-2-furancarboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of methyl 5-methyl-2-furancarboxylate (2.33 g, 16.29 mmol) and aluminum chloride (3.3 g, 24.75 mmol) in chloroform (50 ml) at room temperature was added Br2 (1.1 ml, 21.35 mmol). The resulting solution was stirred at room temperature in a 150 mL sealed tube reactor for 2 hours. Upon completion, the solution was cooled in an ice bath, H2O added and reaction partitioned between CHCl3/H2O. The organic layer was washed with NaHCO3 and then Na2S2O3. The organic layer was dried with Na2SO4, concentrated, adsorbed onto silica and purified via column chromatography (0-20% EtOAc/Hexanes) affording the title compound (2.13 g, 9.72 mmol, 60%): LC-MS (ES) m/z=221 (M+H)+.

Workup

  1. customsealed tube reactor for 2 hours
  2. temperatureUpon completion, the solution was cooled in an ice bath
  3. customreaction
  4. custompartitioned between CHCl3/H2O
  5. washThe organic layer was washed with NaHCO3
  6. dry with materialThe organic layer was dried with Na2SO4
  7. concentrationconcentrated
  8. custompurified via column chromatography (0-20% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-45966bffc41b4c149668b5b652c8b8f6
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

Loading…