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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2096956Generated: October 31, 2026

Ethyl Acetate → 6-bromo-2,3-dihydro-1H-indol-2-one

https://huagongshe.com/reaction/2096956

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
Reactant4-Bromo-2-nitrophenylacetic AcidHCID 271551—
CatalystIronHCID 23925—
SolventAcetic AcidHCID 176—
Product6-bromo-2,3-dihydro-1H-indol-2-oneHCID 277328958%

Reaction Conditions

Temperature100 °C

Reaction Steps

Iron (40.0 g, 700 mmol) was added slowly to a stirred solution of 2-(4-bromo-2-nitrophenyl)acetic acid (preparation 1b, 46.6 g, 200 mmol) in acetic acid (390 mL) at 75° C., and then mixture was stirred for 1 hour at 100° C. Then the mixture was cooled and ethyl acetate was added. The mixture was filtered through Celite® and the solvent evaporated. The crude product was washed with 0.1M aqueous hydrochloric acid, water, diethyl ether and dried to give the title compound (22.0 g, 58%) as a solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08450341B2
Source datasetuspto-grants-2013_05
ORD IDord-88c9bcda499f475eaee45a18a8e34477
Source noteuspto-grants-2013_05