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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 536466Generated: October 31, 2026

Cesium carbonate → HCID 89621860, compound

https://huagongshe.com/reaction/536466

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantBenzophenone imineHCID 136809—
ReactantHCID 89621492HCID 89621492—
CatalystBinap, (A+-)-HCID 634876—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
ProductHCID 89621860HCID 8962186084.4%

Reaction Steps

A solution of Example 25E (950 mg, 4.11 mmol), (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (154 mg, 0.247 mmol), Pd2(dba)3 (11 mg, 0.12 mmol), diphenylmethanimine (1.09 mL, 6.17 mmol) and Cs2CO3 (335 mg, 10.3 mmol) in toluene (20 mL) was heated at 85° C. for 16 hours. The mixture was cooled to ambient temperature, filtered through a layer of Celite, and washed with diethyl ether (60 mL). The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography (gradient elution: 0-20% EtOAc/hexanes) to provide 4-(diphenylmethyleneamino)-5-fluoro-2,3-dihydro-1H-inden-2-ol (1.15 g, 3.47 mmol, 84%) which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08859584B2
Source datasetuspto-grants-2014_10
ORD IDord-b36db20c67e84047a43efecf51e58e26
Source noteuspto-grants-2014_10