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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1788095Generated: October 29, 2026

Acetic Acid → 6-Chloro-9a-(2-fluoroethyl)-7-methoxy-9,9a-dihydro-1H-fluoren-3(2H)-one

https://huagongshe.com/reaction/1788095

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AcidHCID 176—
ReactantPyrrolidineHCID 31268—
ReactantHCID 57603342HCID 57603342—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
Product6-Chloro-9a-(2-fluoroethyl)-7-methoxy-9,9a-dihydro-1H-fluoren-3(2H)-oneHCID 53438179—

Reaction Conditions

Temperature95 °C

Reaction Steps

To a solution of 6-chloro-2-(2-fluoroethyl)-5-methoxy-2-(3-oxobutyl)indan-1-one (32 g, 102 mmol) in toluene (1000 mL) were added acetic acid (7.0 mL, 120 mmol) and pyrrolidine (10 mL, 120 mmol) and the solution was heated at 95° C. for 2 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc (1000 mL), washed with water and saturated aqueous NaHCO3, and dried over MgSO4. Filtration through a pad of silica gel and removal of the solvent under vacuum gave 6-chloro-9a-(2-fluoroethyl)-7-methoxy-1,2,9,9a-tetrahydro-3H-fluoren-3-one as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07511152B2
Source datasetuspto-grants-2009_03
ORD IDord-6fc3ff70fc1145e6965aa98f5831f3c5
Source noteuspto-grants-2009_03