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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1711972Generated: October 30, 2026

Trifluoroacetic acid → 5-(2-Chloroethyl)-6-chlorooxindole

https://huagongshe.com/reaction/1711972

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTrifluoroacetic acidHCID 6422—
ReactantTriethylsilaneHCID 12052—
Reactant5-chloroacetyl-6-chlorooxindoleHCID 3730946—
Product5-(2-Chloroethyl)-6-chlorooxindoleHCID 1060947492.3%

Reaction Conditions

Temperature42.5 °C

Reaction Steps

Triethylsilane (57.2 gm) was added slowly to the reaction mixture of 5-(2-Chloro acetyl) -6-chloro oxindole (50.0 gm) and trifluoroacetic acid (175 mL) below the temperature of 45° C. The reaction was maintained at 40-45° C. for 6 hours. The reaction mass was cooled to 0° C. to -5° C. and maintained stirring for 90 minutes. The separated solid was filtered and washed with water (50 mL). Then the wet compound was further slurred in water (250 mL) for 90 minutes. The resultant solid was filtered, washed with water (50 mL) and dried at a temperature of 70-75° C. to afford 5-(2-chloroethyl) -6-chloro oxindole (43.5 gm).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07790886B2
Source datasetuspto-grants-2010_09
ORD IDord-29d7a05068454bbea4fe71a6b6c44e58
Source noteuspto-grants-2010_09