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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 509458Generated: October 29, 2026

4-Fluorophenol → 7-(4-Fluorophenoxy)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazole

https://huagongshe.com/reaction/509458

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-FluorophenolHCID 9732—
ReactantTriphenylphosphineHCID 11776—
ReactantDiethyl azodicarboxylateHCID 5462977—
ReactantHCID 89545187HCID 89545187—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product7-(4-Fluorophenoxy)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazoleHCID 7155781743.2%

Reaction Conditions

Temperature50 °C

Reaction Steps

To a mixture of 3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazol-7-ol (48 mg, 0.149 mmol) in THF (1.0 mL) was added 4-flurophenol (23 mg, 0.2 mmol), Ph3P (58 mg, 0.22 mmol) and DEAD (39 mg, 0.22 mmol). The reaction mixture was stirred over night at 50° C. The reaction mixture cooled, diluted with EtOAc, washed with water and brine, dried over MgSO4 and concentrated. The crude product was purified by preparative TLC using 5% MeOH in DCM as solvent to afford 27 mg of the title product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09096582B2
Source datasetuspto-grants-2015_08
ORD IDord-b43af41842274b0583e8ac2ffc2ca707
Source noteuspto-grants-2015_08