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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1966497Generated: October 25, 2026

Dimethyl Sulfoxide → Methyl 5,5'-difluoro-2'-nitrobiphenyl-2-carboxylate

https://huagongshe.com/reaction/1966497

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
Reactant2-Bromo-4-fluoro-1-nitrobenzeneHCID 2756993—
ReactantMethyl 2-bromo-4-fluorobenzoateHCID 7210837—
CatalystCopperHCID 23978—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventEthyl AcetateHCID 8857—
ProductMethyl 5,5'-difluoro-2'-nitrobiphenyl-2-carboxylateHCID 67296874113.3%

Reaction Conditions

Temperature100 °C

Reaction Steps

To 2-bromo-4-fluoro-1-nitrobenzene (185.16 mg, 0.842 mmol) was added Pd2dba3 (23.12 mg, 0.025 mmol) and copper powder (271 mg, 4.26 mmol). Dimethylsulfoxide (2.3 ml) and methyl 2-bromo-4-fluorobenzoate (0.122 ml, 0.842 mmol) were added and the mixture was stirred vigorously at 100° C. for 2 h. The mixture was cooled to room temperature, diluted with ethyl acetate (20 ml), and filtered. The filtrate was washed with water and dried (anhydrous Na2SO4) and concentrated to give a yellow oil (279.8 mg). This oil was utilized without purification for the preparation of Example 38b.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08420596B2
Source datasetuspto-grants-2013_04
ORD IDord-e260a73252e14908b3c8a6724e3c06a4
Source noteuspto-grants-2013_04