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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 472990Generated: October 30, 2026

Cesium carbonate → 3-(1-Oxo-1,1',3,3'-tetrahydrospiro[indene-2,2'-phenalene]-6-yl)benzonitrile

https://huagongshe.com/reaction/472990

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant3-Cyanophenylboronic acidHCID 2734325—
Reactant6-bromo-1',3'-dihydrospiro[indene-2,2'-phenalen]-1(3H)-oneHCID 58197044—
CatalystHCID 178418476HCID 178418476—
Solvent1,4-DioxaneHCID 31275—
Product3-(1-Oxo-1,1',3,3'-tetrahydrospiro[indene-2,2'-phenalene]-6-yl)benzonitrileHCID 6658464660%

Reaction Conditions

Temperature100 °C

Reaction Steps

6-Bromo-1′,3′-dihydrospiro[indene-2,2′-phenalen]-1(3H)-one (200 mg, 0.57 mmol) and 3-cyanophenylboronic acid (168 mg, 1.17 mmol) was dissolved in 1,4-dioxane (5 mL), Cs2CO3 (0.6 mL, 2 M) was added. Then Pd(PPh3)2Cl2 (10 mg) was added under N2. The mixture was heated at 100° C. for 10 minutes under microwave. The solvent was removed in vacuum. The crude product was purified by preparative TLC to give 3-(1-oxo-1,1′,3,3′-tetrahydrospiro[indene-2,2′-phenalene]-6-yl)benzonitrile (130 mg, 60%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08633212B2
Source datasetuspto-grants-2014_01
ORD IDord-c8eb20b0b7c34b9189243d43d4c2cad5
Source noteuspto-grants-2014_01