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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1502857Generated: October 31, 2026

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

https://huagongshe.com/reaction/1502857

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 numberUS09211280B2
Source datasetuspto-grants-2015_12
ORD IDord-fe044e3612ca47c595d4bb7f8b37c5a9
Source noteuspto-grants-2015_12