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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1475757Generated: October 25, 2026

Potassium Fluoride → 6-Methyl-3'-trifluoromethyl-biphenyl-3-carboxylic Acid Methyl Ester

https://huagongshe.com/reaction/1475757

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium FluorideHCID 522689—
Reactant3-(Trifluoromethyl)phenylboronic acidHCID 2734388—
ReactantTri-tert-butylphosphine tetrafluoroborateHCID 2734635—
ReactantMethyl 3-bromo-4-methylbenzoateHCID 7015747—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
Solvent1,4-DioxaneHCID 31275—
Product6-Methyl-3'-trifluoromethyl-biphenyl-3-carboxylic Acid Methyl EsterHCID 6716972483.2%

Reaction Conditions

Temperature70 °C

Reaction Steps

3-trifluoromethylphenylboronic acid (278 mg, 1.46 mmol), tris(dibenzylideneacetone)-dipalladium(0) (61 mg, 0.066 mmol), potassium fluoride (255 mg, 4.38 mmol) and tri-tert-butylphosphonium tetrafluoroborate (46 mg, 0.159 mmol) in a flask were thoroughly flushed with argon. 3-bromo-4-methylbenzoic acid methyl ester (304 mg, 1.32 mmol) was added as solution in dioxane (5 ml). the mixture was stirred at 70° C. for 3 h, filtered over silica and evaporated to dryness. The raw material was purified by silica gel chromatography with a hetane/ethyl acetate gradient to yield the title compound (323 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09018383B2
Source datasetuspto-grants-2015_04
ORD IDord-e5946d34e5264b10bd644510e6c7c729
Source noteuspto-grants-2015_04