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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1257436Generated: October 25, 2026

Triphenylphosphine → Methyl 4-bromo-5-methylfuran-2-carboxylate

https://huagongshe.com/reaction/1257436

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriphenylphosphineHCID 11776—
ReactantAmmonium ChlorideHCID 25517—
ReactantMethyl 4,5-Dibromo-2-furancarboxylateHCID 4135083—
ReactantHCID 178477798HCID 178477798—
CatalystPalladium ChlorideHCID 24290—
SolventTetrahydrofuranHCID 8028—
ProductMethyl 4-bromo-5-methylfuran-2-carboxylateHCID 6045441,830.4%

Reaction Steps

To a mixture of the compound (1.80 g) obtained in Example 128a, palladium chloride(II) (0.02 g), triphenylphosphine (0.07 g) and tetrahydrofuran (30 mL) was added MeZnCl (2M tetrahydrofuran solution, 9.5 ml), and the mixture was heated under reflux for 4 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane ethyl acetate) to give the title compound (1.07 g) as a colorless solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08461348B2
Source datasetuspto-grants-2013_06
ORD IDord-5f3bca02527d470a924e211a0b5035a5
Source noteuspto-grants-2013_06