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

HRID 1961274Notes

Reaction equation

HRID 1961274 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-fef9252b0aa74a1a9b6d99010dd545c5
Source dataset
uspto-grants-2013_04
Patent number
US08410158B2

Reaction notes

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