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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1503716Generated: October 31, 2026

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

https://huagongshe.com/reaction/1503716

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 H2O (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 numberUS09212164B2
Source datasetuspto-grants-2015_12
ORD IDord-d40a8525c51f40e3a97c8e25224416e6
Source noteuspto-grants-2015_12