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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 587709Generated: October 28, 2026

Phthalimide potassium salt → 3-Chloro-4-((1,3-dioxoisoindolin-2-yl)methyl)benzaldehyde

https://huagongshe.com/reaction/587709

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPhthalimide potassium saltHCID 24194345—
Reactant4-(Bromomethyl)-3-chlorobenzaldehydeHCID 86675177—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product3-Chloro-4-((1,3-dioxoisoindolin-2-yl)methyl)benzaldehydeHCID 8667517866.7%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a stirred solution of 4-(bromomethyl)-3-chlorobenzaldehyde (3.8 g, 14 mmol) in DMF (40 mL) was added potassium pthalimide (3.54 g, 19.14 mmol), and the mixture was heated at 60° C. for 6 h. The reaction mixture was cooled to ambient temperature and diluted with water (100 mL). The solid obtained was separated by filtration and dried under vacuum to afford the title compound as a white solid (2.8 g, 60%): mp 123-126° C.; 1H NMR (400 MHz, CDCl3) δ 9.95 (s, 1H), 8.21 (s, 1H), 7.91 (m, 3H), 7.80 (m, 2H), 7.20 (m, 1H), 5.05 (s, 2H); ESIMS m/z 298.03 ([M−H]−).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09226501B2
Source datasetuspto-grants-2016_01
ORD IDord-5b04bc457df34c73815566144c6102bd
Source noteuspto-grants-2016_01