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

HRID 2392294Notes

Reaction equation

HRID 2392294 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[Zn][CH3:14]>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[CH3:14]

Participants

5

Reactant 2

HCID 4135083Methyl 4,5-Dibromo-2-furancarboxylateHCID 178477798HCID 178477798, compound

Product 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylateYield 72%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4,5-dibromo-2-furancarboxylate (4.5 g, 15.85 mmol) and BIS(TRIPHENYLPHOSPHINE)PALLADIUM(II) CHLORIDE (0.38 g, 0.541 mmol) in THF (100 mL) at RT was added chloro(methyl)zinc (15 mL, 30 mmol) dropwise. After stirring for 10 h, the reaction was quenched with NH4Cl (sat'd) (50 mL). The mixture was extracted with EtOAc (50 mL×3), and the collected organic layers were dried over MgSO4. Solvent was removed under vacuum and the resulting residue was purified via column chromatography (silica, EtOAc/Hex 10-20%) to give the title compound (2.5 g, 72%) as a white solid: LC-MS (ES) m/z 220 (M+H)+.

Workup

  1. customthe reaction was quenched with NH4Cl (sat'd) (50 mL)
  2. extractionThe mixture was extracted with EtOAc (50 mL×3)
  3. dry with materialthe collected organic layers were dried over MgSO4
  4. customSolvent was removed under vacuum
  5. customthe resulting residue was purified via column chromatography (silica, EtOAc/Hex 10-20%)

Sources & evidence

ORD record
ord-37b3f92a18484714af99fc675f0f2587
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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