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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 858919Generated: November 1, 2026

Toluene → HCID 11389458, compound

https://huagongshe.com/reaction/858919

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantPotassium IodideHCID 4875—
Reactant5-Bromo-1-(4-fluorophenyl)-1,3-dihydroisobenzofuranHCID 11323819—
ReactantHCID 178418546HCID 178418546—
SolventAmmoniaHCID 222—
SolventDimethylformamideHCID 6228—
ProductHCID 11389458HCID 11389458133.3%

Reaction Conditions

Temperature100 °C

Reaction Steps

Potassium iodide (25 g), Copper (I) cyanide (11.8 g) were added to a solution of the [1-(3-dimethylamino)propyl)]-1-(4-fluorophenyl)-1,3-dihydro-5-bromoisobenzofuran (25 g) in dimethylformamide (25 ml). The reaction mixture was heated to 135–145° C. and maintained for 28 hours. The reaction mixture was cooled to 100° C. and poured in ammonia solution containing toluene and stirred for 2 hours to get a clear separation of layers. Then the organic layer after acid base treatment was separated and washed with water twice (2×100 ml), dried with anhydrous sodium sulfate and finally the toluene layer was distilled to get the crude 1-[3-(dimethylamino) propyl]-14-fluorophenyl)-1,3-dihydro-5-isobenzofuran carbonitrile base 16.5 g, with the following HPLC profile.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07148364B2
Source datasetuspto-grants-2006_12
ORD IDord-d83a6ea7a95c42479fc8d7cb56d57e54
Source noteuspto-grants-2006_12