Methanol → Methyl 4,5-Dibromo-2-furancarboxylate

HRID 2392130Notes

Reaction equation

HRID 2392130 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=[O:9])[O:5][C:6]=1[Br:7].S(=O)(=O)(O)O.[CH3:16]O>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:16])=[O:9])[O:5][C:6]=1[Br:7]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 41948324,5-Dibromofuran-2-carboxylic acid

Product 1

HCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateYield 90%

Conditions

Temperature
50 °C

Procedure

To a solution of 4,5-dibromo-2-furancarboxylic acid (25 g, 93 mmol) in methanol (185 ml) was added sulfuric acid (24.7 ml, 463 mmol). The resulting solution stirred at 50° C. over 12 h. The solution was partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried over Na2SO4, concentrated and used directly without further purification providing methyl 4,5-dibromo-2-furancarboxylate (23.67 g, 83 mmol, 90% yield), LCMS (ES) m/e 283, 285, 287 (M, M+2, M+4)+.

Workup

  1. customThe solution was partitioned between H2O-DCM
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried over Na2SO4
  4. concentrationconcentrated
  5. customused directly without further purification

Sources & evidence

ORD record
ord-63f71f8e81ab4484811c03fb3f576368
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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