Methyl 4,5-Dibromo-2-furancarboxylate → Methyl 4-bromo-5-methylfuran-2-carboxylate

HRID 2392241Notes

Reaction equation

HRID 2392241 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1Br.[Cl-].[CH3:13][Zn+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[O:5][C:6]=1[CH3:13]

Participants

5

Reactant 2

HCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178477797HCID 178477797, compound

Product 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylateYield 51%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Methyl 4,5-dibromo-2-furancarboxylate (3.7 g, 13.03 mmol) [prepared according to Example 127] and trans-dichlorobis(triphenylphosphine)Palladium (II) (0.46 g, 0.65 mmol) were combined in THF (50 ml) to give a yellow suspension. A THF solution of methylzinc chloride (11.40 ml, 22.81 mmol) was added dropwise at room temperature. After stirring at ambient temperature for 20 h, the solution was concentrated and purified using silica gel and eluting with 0-30% ethyl acetate/hexane to generate the title compound as a white solid (1.45 g, 6.61 mmol, 51% yield): LC-MS (ES) m/z 220 (M+H)+.

Workup

  1. customto give a yellow suspension
  2. concentrationthe solution was concentrated
  3. custompurified
  4. washeluting with 0-30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-4d8ab741034745d7bc28adc783bd9c80
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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