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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1464870Generated: November 1, 2026

Toluene → HCID 59288845, compound

https://huagongshe.com/reaction/1464870

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium CarbonateHCID 11430—
Reactant3-Tolylboronic acidHCID 2733950—
Reactant2-Chloro-6-fluoroquinolineHCID 15059433—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
ProductHCID 59288845HCID 5928884580.1%

Reaction Conditions

Temperature100 °C

Reaction Steps

3-methylphenyl boronic acid (13 mmol), 2-chloro-6-fluoroquinoline (10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 mmol) and potassium carbonate (15 g) are put in a two-neck round-bottom flask and dissolved in tetrahydrofuran (THF) (30 mL) and H2O (10 mL). Subsequently, the resulting solution is stirred in a bath under a temperature of about 100° C. for 24 hours. After completion of the reaction, THF and toluene are removed. The reaction mixture is extracted with dichloromethane and water, and then being distilled under reduced pressure. The resulting residence is filtered by silica gel column and distilled under reduced pressure again. Next, by re-crystallizing and filtering, 2-(3-methylphenyl)-6-fluoroquinoline (1.9 g) is yielded.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08999476B2
Source datasetuspto-grants-2015_04
ORD IDord-5b12f72d9b2441b2bca2f9e512c732a8
Source noteuspto-grants-2015_04