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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 431582Generated: October 31, 2026

Water → 2-[5-(4-Fluoro-benzyloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetamide

https://huagongshe.com/reaction/431582

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactant2-BromoacetamideHCID 69632—
Reactant5-(4-Fluoro-benzyloxy)-isoindole-1,3-dioneHCID 22397081—
SolventTetrahydrofuranHCID 8028—
Product2-[5-(4-Fluoro-benzyloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-acetamideHCID 1012579865%

Reaction Steps

A mixture of 5-(4-fluoro-benzyloxy)-isoindole-1,3-dione (100 mg, 0.37 mmol), sodium hydride (55% in mineral oil, 18 mg, 0.42 mmol) and 2-bromoacetamide (61 mg, 0.44 mmol) in dry tetrahydrofuran (5 mL) at 0° C. was stirred at room temperature for 3 h and then heated at 50° C. for 1 h. After cooling to 0° C., water (2 mL) was added and the product extracted with ethyl acetate. The organic extracts were then washed with brine and dried over sodium sulfate. Filtration and evaporation gave a residue which was purified by chromatography (SiO2, heptane-CH2Cl2 2:3 then CH2Cl2— 2N NH3—MeOH 99:1: to 4:1) to afford the title compound (78 mg, 65%) as a white solid. MS: m/e=329.3 (M+H+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06660736B2
Source datasetuspto-grants-2003_12
ORD IDord-2bf4cc49c1a340f6bb33e1f15a8d995e
Source noteuspto-grants-2003_12