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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 12388Generated: October 29, 2026

1-Fluoro-2-nitrobenzene → 3,3-Dimethyl-1-(2-nitrophenyl)-2,3-dihydro-1H-indole

https://huagongshe.com/reaction/12388

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-Fluoro-2-nitrobenzeneHCID 73895—
Reactant3,3-DimethylindolineHCID 11804912—
SolventDichloromethaneHCID 6344—
Product3,3-Dimethyl-1-(2-nitrophenyl)-2,3-dihydro-1H-indoleHCID 5933771195%

Reaction Conditions

Temperature175 °C

Reaction Steps

To 2c (317 mg, 2.12 mmol) was added 1-fluoro-2-nitrobenzene (200 mg, 1.42 mmol). The reaction mixture was stirred at 175° C. for 8 h. The reaction mixture was diluted with CH2Cl2 and washed with 1N HCl and dried over Na2SO4. The solvent was evaporated under reduced pressure and purified by column chromatography using 0 to 10% EtOAc in hexane over 30 min as eluting solvent to afford 2d (360 mg, 95%) as an oil. MS (ES) m/z 269 [M+H]+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07728008B2
Source datasetuspto-grants-2010_06
ORD IDord-c8b49cfec5fa471483c52646642798ca
Source noteuspto-grants-2010_06