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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1811006Generated: October 25, 2026

1,3-Isobenzofurandione, 5-fluoro- → 2-(3-Bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dione

https://huagongshe.com/reaction/1811006

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,3-Isobenzofurandione, 5-fluoro-HCID 67572—
Reactant3-Bromo-o-toluidineHCID 123538—
SolventAcetic AcidHCID 176—
Product2-(3-Bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dioneHCID 5937500865.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 3-bromo-2-methylaniline (200 mg, 1.075 mmol) and 5-fluoroisobenzofuran-1,3-dione (179 mg, 1.075 mmol) in acetic acid (2 mL) was heated at 100° C. for 4.5 h. The mixture was concentrated and the residue was purified by column chromatography (eluting with a gradient from hexane to 60:40 hexane-EtOAc) to give 2-(3-bromo-2-methylphenyl)-5-fluoroisoindoline-1,3-dione as a white solid (235 mg, 59%). Mass spectrum m/z 334, 336 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08362065B2
Source datasetuspto-grants-2013_01
ORD IDord-f04cdbdad9294dd4ae86f355737253ae
Source noteuspto-grants-2013_01