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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1052499Generated: October 26, 2026

Water → HCID 64204670, compound

https://huagongshe.com/reaction/1052499

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantPotassium AcetateHCID 517044—
ReactantBis(pinacolato)diboraneHCID 2733548—
Reactant3-Bromo-5-(difluoromethoxy)pyridineHCID 59108568—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
SolventEthyl AcetateHCID 8857—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 64204670HCID 6420467072.2%

Reaction Conditions

Temperature90 °C

Reaction Steps

3-Bromo-5-(difluoromethoxy)pyridine (813 mg, 3.63 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (1.84 g, 7.25 mmol), potassium acetate (1.07 g, 11 mmol), and bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (296 mg, 0.36 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (201 mg, 0.36 mmol) were suspended in dioxane (35 ml) and stirred at 90° C. overnight. After usual work-up with water and ethyl acetate, the reaction crude was purified by reverse phase chromatography (C-18 silica from Waters®, water/1:1 acetonitrile-methanol as eluents [0.1% v/v formic acid buffered] 0% to 100%) to give 495 mg (72% yield) of the title compound as a yellow oil. Purity 95%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09388189B2
Source datasetuspto-grants-2016_07
ORD IDord-d502da218988450bbea55c4306430304
Source noteuspto-grants-2016_07