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

HRID 2088490Notes

Reaction equation

HRID 2088490 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:9][C:8](Br)=[C:7]([Br:11])[CH:6]=1)=[O:4].[CH3:12][Zn]Cl>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>[CH3:1][O:2][C:3]([C:5]1[O:9][C:8]([CH3:12])=[C:7]([Br:11])[CH:6]=1)=[O:4]

Participants

5

Reactant 2

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

Product 1

HCID 604544Methyl 4-bromo-5-methylfuran-2-carboxylateYield 84.8%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dibromo-furan-5-carboxylic acid methyl ester (200 mg, 0.70 mmol) in THF (4 mL) was added Pd(PPh3)2Cl2 (50 mg) and MeZnCl (2 M in THF, 420 μL, 0.84 mmol) at room temperature. The reaction was stirred at this temperature for 12 hr before the solvent was removed. Column chromatography afforded 4-Bromo-5-methyl-furan-2-carboxylic acid methyl ester (130 mg, 84%). Suzuki coupling of 4-Bromo-5-methyl-furan-2-carboxylic acid methyl ester with the corresponding boronic acid (See the synthesis of Example 1, Step B) provided Methyl 4-(4-(2,6-difluorobenzamido)phenyl)-5-methylfuran-2-carboxylate.

Workup

  1. customwas removed

Sources & evidence

ORD record
ord-63391d99fd8447da9e271f9f675494d6
Source dataset
uspto-grants-2013_05
Patent number
US08435996B2

Reaction notes

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